bluuebunny/crossref_metadata_2025 huggingface dataset:
Pentaerythrityl Tetrabromide
Authors: Herzog Hershel L.
Published: November 2003

Pentaerythrityl tetrabromide

product: pentaerythrityl tetrabromide
Phenyldichlorophosphine
Authors: Buchner B. , Lockhart L. B.
Published: November 2003

Phenyldichlorophosphine

product: phenyldichlorophosphine
dl
‐4,4′,6,6′‐Tetrachlorodiphenic Acid
Authors: Atkinson Edward R. , Murphy Donald M. , Lufkin James E.
Published: November 2003

dl
‐4,4′,6,6′‐Tetrachlorodiphenic acid

intermediate: 3,5‐dichloro‐2‐aminobenzoic acid

product: dl‐4,4′,6,6′‐Tetrachlorodiphenic acid.
Triethyl Phosphite
Authors: Ford‐Moore A. H. , Perry B. J.
Published: November 2003

Triethyl phosphite

solvent: 1 l. of dry petroleum ether

product: Triisopropyl phosphite

product: Triethyl phosphite
1,1′‐Azo‐
bis
‐1‐Cyclohexanenitrile
Authors: Overberger C. G. , Huang Pao‐tung , Berenbaum M. B.
Published: November 2003

1,1′‐Azo‐
bis
‐1‐cyclohexanenitrile

product: 2,2′‐Azo‐
bis
‐isobutyronitrile

product: 1,1′‐Azo‐
bis
‐1‐cyclohexanenitrile
p
‐Chlorophenyl Salicylate
Authors: Gaylord Norman G. , Kamath P. M.
Published: November 2003

p
‐Chlorophenyl salicylate

product:
p
‐chlorophenyl salicylate
Cyanogen Iodide
Authors: Bak B. , Hillebert A.
Published: November 2003

Cyanogen iodide

product: cyanogen iodide
Diethyl Ethylidenemalonate
Authors: Fones William S.
Published: November 2003

Diethyl ethylidenemalonate

product: diethyl ethylidenemalonate
4,6‐Dimethylcoumalin
Authors: Smith Newton R. , Wiley Richard H.
Published: November 2003

4,6‐Dimethylcoumalin

product: 4,6‐dimethylcoumalin
2,3‐Diphenylsuccinonitrile
Authors: Davis R. B. , Ward J. A. , McRae J. A. , Bannard R. A. B.
Published: November 2003

2,3‐Diphenylsuccinonitrile

product: 2,3‐diphenylsuccinonitrile
Methyl
p
‐Acetylbenzoate
Authors: Emerson William S. , Deebel George F.
Published: November 2003

Methyl
p
‐acetylbenzoate

reactant: 29–32 g. of unreacted methyl
p
‐ethylbenzoate

product: methyl
p
‐acetylbenzoate

intermediate:
p
‐ethylbenzoic acid
Neophyl Chloride
Authors: Smith W. T. , Sellas J. T.
Published: November 2003

Neophyl chloride

reactant: 201 g. (219 ml., 2.22 moles) of methallyl chloride

product: neophyl chloride

byproduct:
p
‐di(chloro‐
tert
‐butyl)benzene
β‐Tetralone
Authors: Soffer M. D. , Bellis M. P. , Gellerson Hilda E. , Stewart Roberta A.
Published: November 2003

β‐Tetralone

intermediate: β‐tetralone bisulfite

product: β‐tetralone
Diethyl 1,1‐Cyclobutanedicarboxylate
Authors: Mariella Raymond P. , Raube Richard
Published: November 2003

Diethyl 1,1‐cyclobutanedicarboxylate

reactant: 480 g. (3.0 moles) of diethyl malonate

reactant: 472 g. (3.0 moles) of trimethylene chlorobromide

product: cyclobutanecarboxylic acid

product: diethyl 1,1‐cyclobutanedicarboxylate
Diethyl γ‐Oxopimelate
Authors: Emerson W. S. , Longley R. I.
Published: November 2003

Diethyl γ‐oxopimelate

product: diethyl γ‐oxopimelate
2,2‐Dimethylpyrrolidine
Authors: Moffett Robert Bruce
Published: November 2003

2,2‐Dimethylpyrrolidine

product: 2,2‐dimethylpyrrolidine
Itaconyl Chloride
Authors: Feuer Henry , Pier Stanley M.
Published: November 2003

Itaconyl Chloride

product: Itaconyl chloride
3‐Methylcoumarone
Authors: Boehme Werner R.
Published: November 2003

3‐Methylcoumarone

intermediate: ethyl α‐phenoxyacetoacetate

solvent: petroleum ether

intermediate: Ethyl 3‐methylcoumarilate (70 g.)

intermediate: 3‐methylcoumarilic acid

product:
3‐Methylcoumarone

reactant: ethyl α‐chloroacetoacetate
m
‐Nitrobenzazide
Authors: Munch‐Petersen Jon
Published: November 2003

m
‐Nitrobenzazide

intermediate: 185.5 g. (1 mole) of
m
‐nitrobenzoyl chloride in 300 ml. of acetone

product:
m
‐nitrobenzazide

solvent: ligroin

product:
p
‐nitrobenzazide
o
‐Nitrocinnamaldehyde
Authors: Buckles Robert E. , Bellis M. Peter
Published: November 2003

o
‐nitrocinnamaldehyde

product:
o
‐nitrocinnamaldehyde
m‐Nitrostyrene
Authors: Wiley Richard H. , Smith Newton R.
Published: November 2003

m‐Nitrostyrene

reactant: 151 g. (1 mole) ofm‐nitrobenzaldehyde

intermediate:m‐nitrocinnamic acid

product:m‐nitrostyrene

product:o‐nitrocinnamic acid

product:p‐nitrocinnamic acid

product:m‐cyanocinnamic acid

product:o‐chlorocinnamic acid

product:m‐chlorocinnamic acid

product:p‐chlorocinnamic acid

product: 2,4‐dichlorocinnamic acid

product: 3,4‐dichlorocinnamic acid

product:m‐bromocinnamic acid

product:p‐methoxycinnamic acid

product: 3,4‐dimethoxycinnamic acid

product:o‐nitrostyrene

product:p‐nitrostyrene

product: 3‐nitro‐4‐hydroxystyrene

product:o‐chlorostyrene

product:m‐chlorostyrene

product:p‐chlorostyrene

product:m‐bromostyrene

product:o‐methoxystyrene

product:p‐methoxystyrene

product:m‐cyanostyrene

product:p‐formylstyrene
α‐Phenylcinnamic Acid
Authors: Buckles Robert E. , Bremer Keith
Published: November 2003

α‐phenylcinnamic acid

product: α‐phenylcinnamic acid
3‐Phenyl‐1‐Propanol
Authors: Shriner R. L. , Ruby Philip R.
Published: November 2003

3‐phenyl‐1‐propanol

product: 3‐phenyl‐1‐propanol
Pyridine‐N‐oxide
Authors: Mosher Harry S. , Turner Leslie , Carlsmith Allan
Published: November 2003

Pyridine‐N‐oxide

intermediate: pyridine‐N‐oxide hydrochloride

product: pyridine‐N‐oxide
2‐(1‐Pyrrolidyl)Propanol
Authors: Moffett Robert Bruce
Published: November 2003

2‐(1‐Pyrrolidyl)propanol

product: 2‐(1‐Pyrrolidyl)propanol
cis
‐Stilbene
Authors: Buckles Robert E. , Wheeler Norris G.
Published: November 2003

cis
‐Stilbene

reactant: 46.0 g. (0.205 mole) of α‐phenylcinnamic acid

solvent: hexane

product:
cis
‐stilbene
α,β,β‐Triphenylpropionic Acid
Authors: Krimmel C. P. , Thielen L. E. , Brown E. A. , Heidtke W. J.
Published: November 2003

α,β,β‐Triphenylpropionic acid

product: α,β,β‐triphenylpropionic acid
Azelanitrile
Authors: Cope Arthur C. , Cotter Robert J. , Estes Leland L.
Published: November 2003

Azelanitrile

reactant: azelaic acid, 100 g. (0.53 mole)

product: azelanitrile
2‐Chloro‐1,1,2‐Trifluoroethyl Ethyl Ether
Authors: Englund Bruce
Published: November 2003

2‐Chloro‐1,1,2‐trifluoroethyl ethyl ether

product: chlorotrifluoroethyl ethyl ether
Cycloheptanone
Authors: Dauben Hyp J. , Ringold Howard J. , Wade Robert H. , Pearson David L. , Anderson Arthur G. , de Boer J. , Backer H. J.
Published: November 2003

Cycloheptanone

reactant: 245.5 g. (258.5 ml., 2.5 moles) of redistilled cyclohexanone

intermediate: sodium salt of 1‐(nitromethyl)cyclohexanol

intermediate: 1‐(aminomethyl)cyclohexanol

product: cycloheptanone

reactant: Nitromethane

intermediate: acetic acid salt of 1‐(aminomethyl)cyclohexanol
3,4‐Dihydro‐2‐Methoxy‐4‐Methyl‐2H‐Pyran
Authors: Longley Raymond I. , Emerson William S. , Blardinelli Albert J.
Published: November 2003

3,4‐Dihydro‐2‐methoxy‐4‐methyl‐2H‐pyran

product: 3,4‐dihydro‐2‐methoxy‐4‐methyl‐2H‐pyran
9,10‐Dihydrophenanthrene
Authors: Phillips Donald D.
Published: November 2003

9,10‐Dihydrophenanthrene

reactant: phenanthrene

product: 9,10‐dihydrophenanthrene
Diphenyl Succinate
Authors: Daub Guido H. , Johnson William S.
Published: November 2003

Diphenyl succinate

product: diphenyl succinate
Ethyl Chlorofluoroacetate
Authors: Englund Bruce
Published: November 2003

Ethyl chlorofluoroacetate

product: ethyl chlorofluoroacetate
N‐Methyl‐1,2‐Diphenylethylamine and Hydrochloride
Authors: Moffett Robert Bruce
Published: November 2003

N‐methyl‐1,2‐diphenylethylamine and hydrochloride

intermediate:
N
‐
benzylidenemethylamine

product: N‐methyl‐1,2‐diphenylethylamine

product: N‐methyl‐1,2‐diphenylethylamine hydrochloride
p
‐Toluenesulfinyl Chloride
Authors: Kurzer Frederick
Published: November 2003

p
‐Toluenesulfinyl chloride

product:
p
‐toluenesulfinyl chloride
p
‐Tolylsulfonylmethylnitrosamide
Authors: de Boer J. , Backer H. J.
Published: November 2003

p
‐Tolylsulfonylmethylnitrosamide

intermediate: sulfonylmethylamide

solvent: petroleum ether

product:
p
‐tolylsulfonylmethylnitrosamide
o
‐Xylylene Dibromide
Authors: Stephenson Emily F. M.
Published: November 2003

o
‐Xylylene dibromide

reactant:
o
‐Xylene (106 g., 1 mole)

solvent: 100 ml. of boiling 60–68° petroleum ether

product:
o
‐Xylylene dibromide
1‐Acetylcyclohexanol
Authors: Stacy Gardner W. , Mikulec Richard A.
Published: November 2003

1‐Acetylcyclohexanol

product: 1‐acetylcyclohexanol

product: cyclohexanone 2,4‐dinitrophenylhydrazone
p
‐Bromomandelic Acid
Authors: Klingenberg J. J.
Published: November 2003

p
‐bromomandelic acid

intermediate: 89 g. (0.25 mole) of
p
,α,α‐tribromoacetophenone

product:
p
‐chloromandelic acid

product:
p
‐iodomandelic acid

product:
p
‐Bromomandelic acid
Chloro‐p‐Benzoquinone
Authors: Harman R. E.
Published: November 2003

Chloro‐p‐benzoquinone

product: chloro‐p‐benzoquinone

product:p‐benzoquinone

product: 3‐chlorotoluquinone

product: 2,5‐dichloroquinone

product: methoxyquinone
Δ
4
‐Cholesten‐3,6‐dione
Authors: Fieser Louis F.
Published: November 2003

Δ
4
‐Cholesten‐3,6‐dione

product: Δ
4
‐cholesten‐3,6‐dione

byproduct: 3,4‐seco‐Δ
5
‐cholesten‐3,4‐dioic acid
Δ
4
‐Cholesten‐3‐one
Authors: Eastham Jerome F. , Teranishi Roy
Published: November 2003

Δ
4
‐Cholesten‐3‐one

product: Δ
4
‐cholesten‐3‐one

reactant: cholesterol

reactant: cyclohexanone
2‐(Dimethylamino)pyrimidine
Authors: Overberger C. G. , Kogon Irving C. , Minin Ronald
Published: November 2003

2‐(Dimethylamino)pyrimidine

product: 2‐(Dimethylamino)pyrimidine

product: N‐Methylaminopyrimidine
Guanylthiourea
Authors: Kurzer Frederick
Published: November 2003

Guanylthiourea

product: guanylthiourea

byproduct: 2,4‐dithiobiuret
1‐Methyl‐3‐phenylindane
Authors: Rosen Milton J.
Published: November 2003

1‐Methyl‐3‐phenylindane

product: 1‐methyl‐3‐phenylindane

product: 1,1,3‐trimethyl‐3‐phenylindane
Methyl 2‐Thienyl Sulfide
Authors: Cymerman‐Craig J. , Loder J. W.
Published: November 2003

Methyl 2‐thienyl sulfide

product: methyl 2‐thienyl sulfide
β‐Methyl‐δ‐valerolactone
Authors: Longley Raymond I. , Emerson William S.
Published: November 2003

β‐Methyl‐δ‐valerolactone

product: β‐methyl‐δ‐valerolactone
Bischloromethyl Ether
Authors: Buc Saul R.
Published: November 2003

Bischloromethyl ether

product: bischloromethyl ether
1,1‐Dichloro‐2,2‐difluoroethylene
Authors: Sauer J. C.
Published: November 2003

1,1‐Dichloro‐2,2‐difluoroethylene

reactant: 10–15‐ml. portion of a solution consisting of 122.4 g. (0.6 mole) of 1,1,1,2‐tetrachloro‐2,2‐difluoroethane in 50 ml. of methanol

product: 1,1‐dichloro‐2,2‐difluoroethylene
Ethyl Diazoacetate
Authors: Searle N. E.
Published: November 2003

Ethyl diazoacetate

product: ethyl diazoacetate
Putrescine Dihydrochloride
Authors: Smith Peter A. S.
Published: November 2003

Putrescine dihydrochloride

intermediate: adipyl hydrazide

product: putrescine dihydrochloride

byproduct: N,N′‐dicarbethoxyputrescine
Tetrahydrothiophene
Authors: Lawson J. Keith , Easley William K. , Wagner William S.
Published: November 2003

Tetrahydrothiophene

product: tetrahydrothiophene
p
‐Toluenesulfonic Anhydride
Authors: Field L. , McFarland J. W.
Published: November 2003

p
‐Toluenesulfonic anhydride

reactant: 190 g. (1.0 mole) of
p
‐toluenesulfonic acid monohydrate

solvent: 400 ml. of ethylene chloride

product:
p
‐toluenesulfonic anhydride
3‐Benzoylpyridine
Authors: Villani Frank J. , King Mary S.
Published: November 2003

3‐Benzoylpyridine

product: 3‐benzoylpyridine
1‐Diethylamino‐3‐Butanone
Authors: Wilds Alfred L. , Nowak Robert M. , McCaleb Kirtland E.
Published: November 2003

1‐diethylamino‐3‐butanone

product: 1‐diethylamino‐3‐butanone
Ethyl Benzoylacetate
Authors: Straley J. M. , Adams A. C.
Published: November 2003

Ethyl benzoylacetate

unknown: 250 ml. of technical naphtha

product: ethyl benzoylacetate
Glutaric Acid and Glutarimide
Authors: Paris G. , Berlinguet L. , Gaudry R. , English J. , Dayan J. E.
Published: November 2003

Glutaric acid and glutarimide

product: glutaric acid

product: glutarimide

product: N‐bromoglutarimide
n
‐Heptamide
Authors: Guthrie J. L. , Rabjohn Norman
Published: November 2003

n
‐Heptamide

product: Heptamide
Nicotinamide‐1‐Oxide
Authors: Taylor E. C. , Crovetti Aldo J.
Published: November 2003

Nicotinamide‐1‐oxide

product: Nicotinamide‐1‐oxide
Norbornylene
Authors: Meinwald J. , Hudak N. J.
Published: November 2003

Norbornylene

product: norbornylene
Oleoyl Chloride
Authors: Allen C. F. H. , Byers J. R. , Humphlett W. J.
Published: November 2003

Oleoyl chloride

reactant: Seventy grams (0.25 mole) of oleic acid

product: oleoyl chloride

reactant: Palmitic acid

product: Palmitoyl chloride

product: Ricinoleoyl chloride

product: 2,4‐Di‐
tert
‐amylphenoxyacetyl chloride
Pseudopelletierine
Authors: Cope Arthur C. , Dryden Hugh L. , Howell Charles F.
Published: November 2003

Pseudopelletierine

reactant: 64 g. (0.5 mole) of 2‐ethoxy‐3,4‐dihydro‐2H‐pyran

product: pseudopelletierine

product: pseudopelletierine hemihydrate
Stearolic Acid
Authors: Khan N. A. , Deatherage F. E. , Brown J. B.
Published: November 2003

Stearolic Acid

product: stearolic acid

intermediate: stearolamide
ar
‐Tetrahydro‐α‐Naphthol
Authors: Gutsche C. David , Peter Hugo H.
Published: November 2003

ar
‐Tetrahydro‐α‐naphthol

intermediate: 5,8‐dihydro‐1‐naphthol

solvent: 250 ml. of petroleum ether

product:
ar
‐Tetrahydro‐α‐naphthol
2‐Amino‐4‐anilino‐6‐(chloromethyl)‐
s
‐triazine
Authors: Overberger C. G. , Michelotti Francis W.
Published: November 2003

2‐Amino‐4‐anilino‐6‐(chloromethyl)‐
s
‐triazine

product: 2‐amino‐4‐anilino‐6‐(chloromethyl)‐
s
‐triazine

product: 2‐Chloromethyl‐4,6‐diamino‐
s
‐triazine
Dicyclopropyl Ketone
Authors: Curtis Omer E. , Sandri Joseph M. , Crocker Richard E. , Hart Harold
Published: November 2003

Dicyclopropyl ketone

reactant: 344 g. (4.0 moles) of γ‐butyrolactone

byproduct: dibutyrolactone

product: dicyclopropyl ketone

product: 1,7‐dichloro‐4‐heptanone

product: di‐(2‐methylcyclopropyl) ketone
Diethyl Methylenemalonate
Authors: Feely Wayne , Boekelheide V.
Published: November 2003

Diethyl methylenemalonate

product: Diethyl methylenemalonate
5,5‐Dimethyl‐2‐
n
‐Pentyltetrahydrofuran
Authors: Colonge J. , Marey R.
Published: November 2003

5,5‐Dimethyl‐2‐
n
‐Pentyltetrahydrofuran

product: 5,5‐dimethyl‐2‐
n
‐pentyltetrahydrofuran
Diphenylacetaldehyde
Authors: Reif Donald J. , House Herbert O.
Published: November 2003

Diphenylacetaldehyde

reactant: 13.2 ml. (0.1 mole) of boron trifluoride etherate

product: diphenylacetaldehyde

product: 2,4‐dinitrophenylhydrazone
3‐Hydroxytetrahydrofuran
Authors: Wynberg Hans , Bantjes A.
Published: November 2003

3‐Hydroxytetrahydrofuran

product: 3‐hydroxytetrahydrofuran
2‐Methyl‐2,5‐Decanediol
Authors: Colonge J. , Marey R.
Published: November 2003

2‐Methyl‐2,5‐decanediol

product: 2‐methyl‐2,5‐decanediol
2‐Methylenedodecanoic Acid
Authors: Allen C. Freeman , Kalm Max J.
Published: November 2003

2‐Methylenedodecanoic acid

reactant: 30.0 g. (0.140 mole) of 2‐methyldodecanoic acid

intermediate:
tert
‐butyl 2‐methylenedodecanoate

product: 2‐methylenedodecanoic acid

solvent: hexane
Methyl
p
‐Tolyl Sulfone
Authors: Field L. , Clark R. D.
Published: November 2003

Methyl
p
‐tolyl sulfone

reactant: 484 g. (2.54 moles) of
p
‐toluenesulfonyl chloride

reactant: 490 g. (370 ml., 3.88 moles) of dimethyl sulfate

product: methyl
p
‐tolyl sulfone

product: methyl phenyl sulfone
Monobenzalpentaerythritol
Authors: Issidorides C. H. , Gulen R.
Published: November 2003

Monobenzalpentaerythritol

product: monobenzalpentaerythritol

byproduct: dibenzalpentaerythritol
Monobromopentaerythritol
Authors: Wawzonek S. , Matar A. , Issidorides C. H.
Published: November 2003

Monobromopentaerythritol

product: monobromopentaerythritol
Monovinylacetylene
Authors: Hennion G. F. , Price Charles C. , McKeon Thomas F.
Published: November 2003

Monovinylacetylene

product: monovinylacetylene
1‐Nitroöctane
Authors: Kornblum N. , Ungnade H. E.
Published: November 2003

1‐Nitroöctane

reactant: 1‐Bromoöctane (96.5 g., 0.5 mole)

reactant: silver nitrite (116 g., 0.75 mole)

byproduct: 1‐octyl nitrite

product: 1‐nitroöctane
N‐(
p
‐Acetylaminophenyl)rhodanine
Authors: Strube R. E.
Published: November 2003

N‐(
p
‐acetylaminophenyl)rhodanine

product: N‐(
p
‐acetylaminophenyl)rhodanine
2,5‐Diamino‐3,4‐dicyanothiophene
Authors: Middleton W. J.
Published: November 2003

2,5‐Diamino‐3,4‐dicyanothiophene

product: 2,5‐diamino‐3,4‐dicyanothiophene
Indazole
Authors: Ainsworth C.
Published: November 2003

Indazole

intermediate: 2‐hydroxymethylenecyclohexanone

solvent: 100 ml. of hot petroleum ether

intermediate: 4,5,6,7‐tetrahydroindazole

product: indazole
Methyl 3‐Methyl‐2‐furoate
Authors: Burness D. M.
Published: November 2003

Methyl 3‐methyl‐2‐furoate

reactant: 3‐ketobutyraldehyde dimethyl acetal

product: methyl 3‐methyl‐2‐furoate
β‐Methyl‐β‐phenyl‐α,α′‐dicyanoglutarimide
Authors: McElvain S. M. , Clemens David H.
Published: November 2003

β‐Methyl‐β‐phenyl‐α,α′‐dicyanoglutarimide

product: β‐Methyl‐β‐phenyl‐α,α′‐dicyanoglutarimide
1‐Phenyl‐1‐Penten‐4‐yn‐3‐ol
Authors: Skattebøl Lars , Jones E. R. H. , Whiting Mark C.
Published: November 2003

1‐Phenyl‐1‐penten‐4‐yn‐3‐ol

solvent: petroleum ether

product: 1‐Phenyl‐1‐penten‐4‐yn‐3‐ol
p
‐Tricyanovinyl‐N,N‐dimethylaniline
Authors: McKusick B. C. , Melby L. R.
Published: November 2003

p
‐Tricyanovinyl‐N,N‐dimethylaniline

product:
p
‐Tricyanovinyl‐N,N‐dimethylaniline
Deoxyanisoin
Authors: Carter P. H. , Craig J. Cymerman , Lack Ruth E. , Moyle M.
Published: November 2003

Deoxyanisoin

product: deoxyanisoin

product: deoxybenzoin

product: deoxypiperoin
Diethyl Aminomalonate Hydrochloride
Authors: Hartung Walter H. , Beaujon Jan H. R. , Cocolas George
Published: November 2003

Diethyl aminomalonate hydrochloride

reactant: 50 g. of diethyl malonate

product: diethyl aminomalonate hydrochloride
Diethyl Bis(hydroxymethyl)malonate
Authors: Block Paul
Published: November 2003

Diethyl bis(hydroxymethyl)malonate

product: diethyl bis(hydroxymethyl)malonate
2,4‐Dinitroiodobenzene
Authors: Bunnett J. F. , Conner R. M.
Published: November 2003

2,4‐Dinitroiodobenzene

solvent: 500 ml. of a mixture of 75% (375 ml.) of petroleum ether

product: 2,4‐Dinitroiodobenzene
2‐Hydroxyisophthalic Acid
Authors: Todd David , Martell A. E.
Published: November 2003

2‐Hydroxyisophthalic acid

product: 2‐hydroxyisophthalic acid monohydrate

product: 2‐hydroxyisophthalic acid
Methylenecyclohexane
Authors: Wittig George , Schoellkopf U.
Published: November 2003

Methylenecyclohexane

intermediate:
Triphenylmethylphosphonium bromide

product: methylenecyclohexane
1‐Methylindole
Authors: Potts K. T. , Saxton J. E.
Published: November 2003

1‐Methylindole

product: 1‐Methylindole
2,6‐Naphthalenedicarboxylic Acid
Authors: Raecke Bernhard , Schirp Hubert
Published: November 2003

2,6‐Naphthalenedicarboxylic acid

intermediate: dipotassium naphthalate

product: 2,6‐Naphthalenedicarboxylic acid

reactant: 1,8‐naphthalic anhydride, m.p. 274–275°, is obtainable from Coaltar Chemicals Corp., 420 Lexington Ave., New York, N. Y.

product: terephthalic acid

product: 2,5‐pyridinedicarboxylic acid
N‐β‐Naphthylpiperidine
Authors: Bunnett J. F. , Brotherton T. K. , Williamson S. M.
Published: November 2003

N‐β‐Naphthylpiperidine

reactant: piperidine

solvent: petroleum ether (boiling range 30–60°)

product: N‐β‐naphthylpiperidine

product: N‐phenylpiperidine

product: N‐α‐naphthylpiperidine
m
‐Nitrophenyl Disulfide
Authors: Sheppard W. A.
Published: November 2003

m
‐Nitrophenyl disulfide

product:
m
‐nitrophenyl disulfide
2,2,5,5‐Tetramethyltetrahydro‐3‐ketofuran
Authors: Newman Melvin S. , Reichle Walter R.
Published: November 2003

2,2,5,5‐Tetramethyltetrahydro‐3‐ketofuran

product: 2,2,5,5‐tetramethyltetrahydro‐3‐ketofuran
2,4,5‐Triaminonitrobenzene
Authors: Boyer J. H. , Buriks R. S.
Published: November 2003

2,4,5‐Triaminonitrobenzene

intermediate:
1,5‐Dichloro‐2,4‐dinitrobenzene

intermediate:
1,5‐Diamino‐2,4‐dinitrobenzene

product:
2,4,5‐Triaminonitrobenzene
1,2,4‐Triazole
Authors: Ainsworth C.
Published: November 2003

1,2,4‐Triazole

intermediate:
1‐Formyl‐3‐thiosemicarbazide

intermediate:
1,2,4‐Triazole‐3(5)‐thiol

product: 1,2,4‐Triazole
4,4′‐Bis(Dimethylamino)Benzil
Authors: Tüzün Celal , Ogliaruso Michael , Becker Ernest I.
Published: November 2003

4,4′‐Bis(Dimethylamino)Benzil

product: 4,4′‐bis(dimethylamino)benzil

byproduct: Crystal Violet

product: 4,4′‐bis(diethylamino)benzil

product: 4,4′‐bis(di‐
n
‐propylamino)benzil
Diazomethane
Authors: Moore James A. , Reed Donald E.
Published: November 2003

Diazomethane

product: diazomethane
4,6‐Dimethyl‐1‐Hepten‐4‐ol
Authors: Seyferth Dietmar , Weiner Michael A.
Published: November 2003

4,6‐Dimethyl‐1‐hepten‐4‐ol

byproduct: tetraphenyltin

product: 4,6‐Dimethyl‐1‐hepten‐4‐ol

reactant: Allyltriphenyltin
Diphenaldehydic Acid
Authors: Bailey Philip S. , Erickson Ronald E.
Published: November 2003

Diphenaldehydic acid

intermediate: 10 g. (0.0368 mole) of 3,8‐dimethoxy‐4,5,6,7‐dibenzo‐1,2‐dioxacycloöctane

product: diphenaldehydic acid

product: methyl ester of diphenaldehydic acid

product: diphenic acid
1,3,5‐Hexatriene
Authors: Hwa Jesse C. H. , Sims Homer
Published: November 2003

1,3,5‐Hexatriene

reactant: 351.0 g. (2.90 moles) of allyl bromide

intermediate: 1,5‐hexadien‐3‐ol

intermediate: bromohexadiene

product: 1,3,5‐hexatriene

product: 3‐Bromo‐1,5‐hexadiene

product: 1‐Bromo‐2,5‐hexadiene
2‐Methyl‐1,3‐Cyclohexanedione
Authors: Mekler A. B. , Ramachandran S. , Swaminathan S. , Newman Melvin S.
Published: November 2003

2‐Methyl‐1,3‐cyclohexanedione

product: 2‐methyl‐1,3‐cyclohexanedione
3‐Methylheptanoic Acid
Authors: Munch‐Petersen Jon
Published: November 2003

3‐Methylheptanoic acid

intermediate:
sec
‐butyl crotonate

product:
sec
‐butyl 3‐methylheptanoate

product: 3‐methylheptanoic acid

product:
sec
‐butyl acrylate

product:
sec
‐butyl methacrylate

product:
sec
‐butyl tiglate

product:
sec
‐butyl β,β‐dimethylacrylate

product:
sec
‐butyl cinnamate

intermediate: methyl α,γ‐di‐(2‐hexyl)‐acetoacetate [methyl 2‐(2′‐hexyl)‐3‐keto‐5‐methylonanoate]

byproduct: di‐
sec
‐butyl α‐(2‐hexyl)‐β‐methylglutarate
2,3,4,5,6‐Penta‐O‐acetyl‐
D
‐gluconic Acid and 2,3,4,5,6‐Penta‐O‐acetyl‐
D
‐gluconyl Chloride
Authors: Braun Charles E. , Cook Clinton D.
Published: November 2003

2,3,4,5,6‐Penta‐O‐acetyl‐
D
‐gluconic acid and 2,3,4,5,6‐penta‐O‐acetyl‐
D
‐gluconyl chloride

reactant: 50 g. (0.28 mole) of
D
‐glucono‐δ‐lactone

intermediate: 2,3,4,6‐tetra‐O‐acetyl‐
D
‐gluconic acid monohydrate

solvent: petroleum ether

product: 2,3,4,5,6‐penta‐O‐acetyl‐
D
‐gluconic acid

product: 2,3,4,5,6‐penta‐O‐acetyl‐
D
‐gluconyl chloride
Phenyl
t
‐Butyl Ether, Method
II
Authors: Sahyun Melville R. V. , Cram Donald J.
Published: November 2003

Phenyl
t
‐butyl ether, Method II

product: phenyl
t
‐butyl ether
o
‐Tolyl Isocyanide
Authors: Ugi Ivar , Meyr Rudolf
Published: November 2003

o
‐Tolyl Isocyanide

reactant: One hundred grams (2.6 g. atoms) of potassium

product:
o
‐Tolyl isocyanide

solvent: 300 ml. of petroleum ether

reactant: N‐
o
‐tolylformamide

: phenyl

: p‐tolyl

: 2,6‐dimethylphenyl

: mesityl

: o‐chlorophenyl

: p‐chlorophenyl

: 2‐chloro‐6‐methylphenyl

: p‐methoxyphenyl

: p‐diethylaminophenyl

: p‐nitrophenyl

: 2‐naphthyl
2‐Allylcyclohexanone
Authors: Howard W. L. , Lorette N. B.
Published: November 2003

2‐Allylcyclohexanone

solvent: 150 g. of toluene

product: 2‐allylcyclohexanone

byproduct: allyl alcohol
N‐Benzylacrylamide
Authors: Parris Chester L.
Published: November 2003

N‐Benzylacrylamide

product: N‐benzylacrylamide

reactant: Commercial acrylonitrile from American Cyanamid Company

product: N‐benzylacetamide

product: N‐(2,4‐dimethylbenzyl)‐acetamide

product: N‐(4‐methoxybenzyl)‐acetamide

product: N,N′‐diacrylyl‐
p
‐xylene‐α‐α′‐diamine

product: N,N′‐diacetyl‐4,6‐dimethyl‐
m
‐xylene‐α,α′‐diamine
1,2‐Bis(
n
‐butylthio)benzene
Authors: Adams Roger , Reifschneider Walter , Ferretti Aldo
Published: November 2003

1,2‐Bis(
n
‐butylthio)benzene

intermediate: cuprous
n
‐butylmercaptide

product:
1,2‐Bis(n‐butylthio)benzene
.

product: 1,4‐bis‐(
n
‐butylthio)benzene

product: 1,2‐bis(phenylthio)benzene

product: 1,4‐bis(phenylthio)benzene
Cyclohexanone Diallyl Acetal
Authors: Howard W. L. , Lorette N. B.
Published: November 2003

Cyclohexanone diallyl acetal

product: cyclohexanone diallyl acetal

byproduct: 2‐allylcyclohexanone
2‐Cyclopentene‐1,4‐Dione
Authors: Rasmusson Gary H. , House Herbert O. , Zaweski Edward F. , DePuy Charles H.
Published: November 2003

2‐Cyclopentene‐1,4‐dione

product: 2‐cyclopentene‐1,4‐dione
Dihydroxycyclopentene
Authors: Korach M. , Nielsen D. R. , Rideout W. H.
Published: November 2003

Dihydroxycyclopentene

product: 3‐cyclopentene‐1,2‐diol

product: 2‐cyclopentene‐1,4‐diol
Ethylene Sulfide
Authors: Searles Scott , Lutz Eugene F. , Hays High R. , Mortensen Harley E.
Published: November 2003

Ethylene sulfide

product: Ethylene sulfide

reactant: Ethylene carbonate obtained from the Eastman Kodak Company or the Jefferson Chemical Company
Indazole
Authors: Huisgen Rolf , Bast Klaus
Published: November 2003

Indazole

product: indazole
3‐Methylpentane‐2,4‐Dione
Authors: Johnson A. W. , Markham E. , Price R.
Published: November 2003

3‐Methylpentane‐2,4‐dione

product: 3‐methylpentane‐2,4‐dione
2‐Norbornanone
Authors: Kleinfelter Donald C. , Schleyer Paul von R.
Published: November 2003

2‐Norbornanone

reactant: 800 g. (17.4 4 moles) of 98–100% formic acid

intermediate: 2‐
exo
‐norbornyl formate

product: 2‐Norbornanone

product: 2‐
exo
‐norborneol
[2.2]Paracyclophane
Authors: Winberg H. E. , Fawcett F. S.
Published: November 2003

[2.2]Paracyclophane

reactant: 100 g. (0.54 mole) of α‐bromo‐p‐xylene

intermediate:p‐methylbenzyltrimethylammonium bromide

product: [2.2]paracyclophane

product: 5,5′‐ethylene‐1,2‐bis‐(2‐thienyl)‐ethane

product: 5,5′‐ethylene‐1,2‐bis‐(2‐furyl)‐ethane
1‐Phenyl‐2‐thiobiuret
Authors: Kurzer Frederick , Tertiuk W.
Published: November 2003

1‐Phenyl‐2‐thiobiuret

intermediate: 1‐phenyl‐2‐thio‐4‐methylisobiuret

solvent: petroleum ether

product: 1‐phenyl‐2‐thiobiuret

product: 1‐phenyl‐2‐thio‐4‐ethylisobiuret
Tetrahydroxyquinone
Authors: Fatiadi A. J. , Sager W. F.
Published: November 2003

Tetrahydroxyquinone

intermediate: sodium salt of tetrahydroxyquinone

product: tetrahydroxyquinone

solvent: petroleum ether
1‐Chloro‐1,4,4‐trifluorobutadiene
Authors: Putnam R. E. , Anderson B. C. , Sharkey W. H.
Published: November 2003

1‐Chloro‐1,4,4‐trifluorobutadiene

intermediate: 2‐chloro‐2,3,3‐trifluorocyclobutyl acetate

product: 1‐chloro‐1,4,4‐trifluorobutadiene
1,4‐Dihydrobenzoic Acid
Authors: Kuehne M. E. , Lambert B. F.
Published: November 2003

1,4‐Dihydrobenzoic acid
Dimethyl 3‐Methylenecyclobutane‐1,2‐Dicarboxylate
Authors: Stevenson H. B. , Cripps H. N. , Williams J. K.
Published: November 2003

Dimethyl 3‐methylenecyclobutane‐1,2‐dicarboxylate

reactant: 250 g. of maleic anhydride

intermediate: 3‐methylenecyclobutane‐1,2‐dicarboxylic anhydride

byproduct: 2–5% of propargylsuccinic anhydride

product: dimethyl 3‐methylenecyclobutane‐1,2‐dicarboxylate
Docosanedioic Acid
Authors: Hünig S. , Lücke E. , Brenninger W.
Published: November 2003

Docosanedioic acid

reactant: 120 g. (0.50 mole) of sebacoyl chloride

intermediate: 2,2′‐sebacoyldicyclohexanone

intermediate: disodium 7,16‐diketodocosanedioate

product: docosanedioic acid

reactant: 150 g. (0.74 mole) of sebacic acid

product: 7,16‐diketodocosanedioic acid

product: eicosanedioic acid

product: tetradecanedioic acid

product: hexadecanedioic acid

product: heptadecanoic acid

product: triacontanoic acid

product: pentatricontanedioic acid
2‐Hydroxythiophene
Authors: Frisell C. , Lawesson S.‐O.
Published: November 2003

2‐Hydroxythiophene

intermediate: 2‐
t
‐butoxythiophene

product: 2‐Hydroxythiophene

byproduct: benzoic acid
Iodosobenzene Diacetate
Authors: Sharefkin J. G. , Saltzman H.
Published: November 2003

Iodosobenzene diacetate

product: iodosobenzene diacetate
Methyl Butadienoate
Authors: Stevenson H. B. , Sharkey W. H.
Published: November 2003

Methyl butadienoate

reactant: 184 g. (1.00 mole) of dimethyl 3‐methylenecyclobutane‐1,2‐dicarboxylate

byproduct: methyl acrylate

product: methyl butadienoate
3‐Methyl‐1‐Phenylphospholene Oxide
Authors: McCormack W. B.
Published: November 2003

3‐Methyl‐1‐phenylphospholene oxide

product: 3‐methyl‐1‐phenyl‐1‐phospha‐3‐cyclopentene 1‐oxide
4‐Methylpyrimidine
Authors: Bredereck H.
Published: November 2003

4‐Methylpyrimidine

product: 4‐methylpyrimidine
N‐Nitromorpholine
Authors: Freeman Jeremiah P. , Shepard Inella G.
Published: November 2003

N‐Nitromorpholine

intermediate: acetone cyanohydrin nitrate

product: N‐nitromorpholine
4‐Nitro‐2,2,4‐Trimethylpentane
Authors: Kornblum Nathan , Jones Willard J.
Published: November 2003

4‐Nitro‐2,2,4‐trimethylpentane

reactant: 25.8 g. (0.20 mole) of 4‐amino‐2,2,4‐trimethylpentane (
tert
‐octylamine)

product: 4‐nitro‐2,2,4‐trimethylpentane

product: 2‐Nitro‐2‐methylpropane

product: 2‐Nitro‐2,3‐dimethylbutane

product: 2‐Nitro‐2,4‐dimethylpentane

product: 1‐Nitro‐1‐methylcyclopentane

product: 1‐Nitro‐1‐methylcyclohexane

product: 1‐Nitro‐1,4‐dimethylcyclohexane

product: 1,8‐Dinitro‐
p
‐methane
4‐Pyridinesulfonic Acid
Authors: Evans Russell F. , Brown Herbert C. , van der Plas H. C.
Published: November 2003

4‐Pyridinesulfonic acid

intermediate: N‐(4‐pyridyl)pyridinium chloride hydrochloride

product: 4‐pyridinesulfonic acid
o
‐Anisaldehyde
Authors: Sisti A. J.
Published: November 2003

o
‐Anisaldehyde

intermediate: 4‐dimethylamino‐2′‐methoxybenzhydrol

byproduct: 2,4‐dinitrophenylhydrazone

product:
o
‐anisaldehyde
t
‐Butyl carbazate
Authors: Carpino Louis A. , Collins David , Göwecke Siegfried , Mayo Joe , Thatte S. D. , Tibbetts Fred , Carpino Louis A. , Carpino Barbara A. , Giza Chester A. , Murray Robert W. , Santilli Arthur A. , Terry Paul H.
Published: November 2003

t
‐Butyl carbazate

solvent: 430 ml. (422 g., 5.33 moles) of pyridine

reactant: 508 ml. (395 g., 5.33 moles) of
t
‐butyl alcohol

reactant: 536 g. (4.85 moles) of methyl chlorothiolformate

intermediate: 500 g. (3.47 moles) of
t
‐butyl S‐methylthiolcarbonate

solvent: 50‐50 mixture of low‐ (b.p. 30–60°) and high‐boiling (b.p. 60–70°) ligroin

reactant: 430 g. (3.33 moles) of quinoline

reactant: 520 g. (3.32 moles) of phenyl chloroformate

intermediate: 388.4 g. (2.0 moles) of phenyl
t
‐butyl carbonate

solvent: petroleum ether

product:
t
‐Butyl carbazate

product: bibenzyl
2,3‐Diaminopyridine
Authors: Fox B. A. , Threlfall T. L.
Published: November 2003

2,3‐Diaminopyridine

reactant: 282 g. (3.0 moles) of 2‐aminopyridine

intermediate: 2‐amino‐5‐bromopyridine

solvent: 500‐ml. portions of hot petroleum ether

intermediate: 2‐amino‐5‐bromo‐3‐nitropyridine

intermediate: 2,3‐Diamino‐5‐bromopyridine

product: 2,3‐diaminopyridine
2,4‐Dinitrobenzenesulfenyl Chloride
Authors: Kharasch Norman , Langford Robert B.
Published: November 2003

2,4‐Dinitrobenzenesulfenyl chloride

reactant: 202 g. (1.00 mole) of 2,4‐dinitrochlorobenzene

intermediate: 2,4‐dinitrophenyl benzyl sulfide

solvent: 3–4 volumes of dry petroleum ether

product: 2,4‐dinitrobenzenesulfenyl chloride

reactant: practical grade 2,4‐dinitrochlorobenzene

product: 2,4‐Dinitrobenzenesulfenyl bromide
Diphenyl Ketimine
Authors: Pickard P. L. , Tolbert T. L.
Published: November 2003

Diphenyl ketimine

product: diphenyl ketimine
N‐Methylbutylamine
Authors: Lucier John J. , Harris Arlo D. , Korosec Philip S.
Published: November 2003

N‐methylbutylamine

product: N‐Methylbutylamine
N‐Methylethylamine
Authors: Wawzonek S. , McKillip W. , Peterson C. J.
Published: November 2003

N‐methylethylamine

intermediate: N‐benzylideneethylamine

product:
N
‐
Methylethylamine

product: N‐methylisopropylamine

product: N‐methylisobutylamine

product: N‐methyl‐
tert
‐butylamine

product: N‐methyl‐2‐methoxyethylamine
3‐Quinuclidone Hydrochloride
Authors: Daeniker H. U. , Grob C. A.
Published: November 2003

3‐Quinuclidone hydrochloride

intermediate: 1‐carbethoxymethyl‐4‐carbethoxypyridinium bromide

intermediate: 1‐carbethoxymethyl‐4‐carbethoxypiperidine

product: 3‐quinuclidone hydrochloride
D,L‐10‐Camphorsulfonic Acid (Reychler's Acid)
Authors: Bartlett Paul D. , Knox L. H.
Published: November 2003

D,L‐10‐Camphorsulfonic acid (Reychler's acid)

product:D,L‐10‐Camphorsulfonic acid
Cycloöctanone
Authors: Eisenbraun E. J.
Published: November 2003

Cycloöctanone

product: cycloöctanone

product: 2‐cyclohexenone
Dichloromethylenetriphenylphosphorane and β,β‐Dichloro‐
p
‐Dimethylaminostyrene
Authors: Speziale A. J. , Ratts K. W. , Bissing D. E.
Published: November 2003

Dichloromethylenetriphenylphosphorane and β,β‐dichloro‐
p
‐dimethylaminostyrene

product: β,β‐
Dichloro‐p‐dimethylaminostyrene
Ethyl γ‐Bromobutyrate
Authors: Lavety J. , Proctor G. R.
Published: November 2003

Ethyl γ‐Bromobutyrate

product: ethyl γ‐bromobutyrate
Glycine
t
‐Butyl Ester
Authors: Moore A. T. , Rydon H. N.
Published: November 2003

Glycine
t
‐butyl ester

intermediate: 28.9 g. (0.18 mole) of
t
‐butyl azidoacetate

intermediate: glycine
t
‐butyl ester phosphite

product: glycine
t
‐butyl ester
Levopimaric Acid
Authors: Lloyd Winston D. , Hedrick Glen W.
Published: November 2003

Levopimaric acid

intermediate: 2‐amino‐2‐methyl‐1‐propanol salt of levopimaric acid

product: levopimaric acid

reactant: 2‐amino‐2‐methyl‐1‐propanol, m.p. 25–29°, N.E. 88.5–99.0, was obtained from the Commercial Solvents Corporation
Nortricyclanol
Authors: Meinwald J. , Crandall J. , Hymans W. E.
Published: November 2003

Nortricyclanol

intermediate: nortricyclyl acetate and bicyclo[2.2.1]hepta‐5‐en‐2‐yl acetate

byproduct: nitrosyl chloride adduct

intermediate: nortricyclyl acetate

product: nortricyclanol
Δ
1(9)
‐Octalone‐2
Authors: Augustine Robert L. , Caputo Joseph A.
Published: November 2003

Δ
1(9)
‐Octalone‐2

intermediate: Δ
1(9)
‐
Octalone‐2
and Δ
9(10)
‐
octalone‐2

product: Δ
1(9)
‐octalone‐2

byproduct: Δ
9(10)
‐octalone‐2
Phenylbromoethyne
Authors: Miller Sidney I. , Ziegler Gene R. , Wieleseck R.
Published: November 2003

Phenylbromoethyne

product: phenylbromoethyne
Phenyl
t
‐Butyl Ether, Method
I
Authors: Frisell Christer , Lawesson Sven‐Olov
Published: November 2003

Phenyl
t
‐butyl ether, Method I

product: phenyl
t
‐butyl ether

byproduct: benzoic acid
Styrylphosphonic Dichloride
Authors: Schmutzler R.
Published: November 2003

Styrylphosphonic dichloride

product: styrylphosphonic dichloride
2,2′‐Bipyridine
Authors: Sasse W. H. F.
Published: November 2003

2,2′‐Bipyridine

solvent: 100 ml. of boiling petroleum ether

product: 2,2′‐bipyridine

byproduct: 2,2′‐pyrrolylpyridine
2‐Bromo‐4‐Methylbenzaldehyde
Authors: Jolad S. D. , Rajagopalan S.
Published: November 2003

2‐Bromo‐4‐methylbenzaldehyde

product: 2‐Bromo‐4‐methylbenzaldehyde
α‐Chloroacetyl Isocyanate
Authors: Speziale A. John , Smith Lowell R.
Published: November 2003

α‐Chloroacetyl isocyanate

product: α‐chloroacetyl isocyanate
Chlorosulfonyl Isocyanate
Authors: Graf Roderich
Published: November 2003

Chlorosulfonyl isocyanate

product: chlorosulfonyl isocyanate
2‐Fluoroheptanoic Acid
Authors: Dean F. H. , Amin J. H. , Pattison F. L. M.
Published: November 2003

2‐Fluoroheptanoic acid

intermediate: 2‐fluoroheptyl acetate

product: 2‐fluoroheptanoic acid
10‐Methyl‐10,9‐Borazarophenanthrene
Authors: Dewar M. J. S. , Dewar R. B. K. , Gaibel Z. L. F.
Published: November 2003

10‐Methyl‐10,9‐borazarophenanthrene

intermediate: 10‐hydroxy‐10,9‐borazarophenanthrene

intermediate: bis(10,9‐borazarophenanthryl) ether

product:
10‐Methyl‐10,9‐borazarophenanthrene

intermediate: 10‐methyl‐10,9‐borazarophenanthrene, bis(10,9‐borazarophenanthryl) ether

solvent: 4 l. of petroleum ether

reactant: Boron trichloride
2‐Phenyl‐3‐
n
‐propylisoxazolidine‐4,5‐
cis
‐dicarboxylic acid N‐phenylimide
Authors: Brüning Ingrid , Grashey Rudolf , Hauck Hans , Huisgen Rolf , Seidl Helmut
Published: November 2003

2‐Phenyl‐3‐
n
‐propylisoxazolidine‐4,5‐
cis
‐dicarboxylic acid N‐phenylimide

product: 2‐phenyl‐3‐
n
‐propylisoxazolidine‐4,5‐
cis
‐dicarboxylic acid N‐phenylimide
Phenyl(trichloromethyl)mercury
Authors: Logan Ted J.
Published: November 2003

Phenyl(trichloromethyl)mercury

product: Phenyl(trichloromethyl)mercury
1,2,3,4‐Tetraphenylnaphthalene
Authors: Fieser Louis F. , Haddadin Makhluf J.
Published: November 2003

1,2,3,4‐Tetraphenylnaphthalene

intermediate:
Diphenyliodonium‐2‐carboxylate

intermediate: diphenyliodonium‐2‐carboxylate monohydrate

solvent: 60 ml. of diethylbenzene

byproduct: iodobenzene

solvent: trimethylene glycol dimethyl ether

solvent:
o
‐Dichlorobenzene

solvent: Diethyl oxalate

solvent: N,N‐dimethylacetamide

product: 1,2,3,4‐Tetraphenylnaphthalene
2,6,6‐Trimethyl‐2,4‐Cyclohexadienone
Authors: Curtin David Y. , Stein Allan R.
Published: November 2003

2,6,6‐Trimethyl‐2,4‐Cyclohexadienone

intermediate: lithium 2,6‐dimethylphenoxide

byproduct: 2,6‐dimethylanisole

product: 2,6,6‐trimethyl‐2,4‐cyclohexadienone
Trimethyloxonium Fluoborate
Authors: Meerwein H.
Published: November 2003

Trimethyloxonium Fluoborate

product: trimethyloxonium fluoborate
trans
‐4‐
t
‐Butylcyclohexanol
Authors: Eliel E. L. , Martin R. J. L. , Nasipuri D.
Published: November 2003

trans
‐4‐
t
‐Butylcyclohexanol

product:
trans
‐4‐
t
‐Butylcyclohexanol

solvent: 150 ml. of hot petroleum ether
2‐Carbethoxycyclooctanone
Authors: Krapcho A. Paul , Diamanti Joseph , Cayen Charles , Bingham Richard
Published: November 2003

2‐Carbethoxycyclooctanone

product: 2‐carbethoxycyclooctanone

product: 2‐carbethoxycyclohexanone

product: 2‐carbethoxycycloheptanone
Cholane‐24‐al
Authors: Moffatt John G.
Published: November 2003

Cholane‐24‐al

reactant: 1.85 g. (9 mmoles) of dicyclohexylcarbodiimide

byproduct: dicyclohexylurea

product: cholane‐24‐al
m
‐Cymene
Authors: Pearson D. E. , Wysong Robert D. , Finkel J. M.
Published: November 2003

m
‐Cymene

product:
m
‐cymene
β,β‐Difluorostyrene
Authors: Fuqua Samuel A. , Duncan Warren G. , Silverstein Robert M.
Published: November 2003

β,β‐Difluorostyrene

product: β,β‐difluorostyrene
Dichloromethyl Methyl Ether
Authors: Gross H. , Rieche A. , Höft E. , Beyer E.
Published: November 2003

Dichloromethyl methyl ether

product: dichloromethyl methyl ether
cis
‐ and
trans
‐1,2‐Divinylcyclobutane
Authors: DeBoer Charles D. , Turro Nicholas J. , Hammond George S.
Published: November 2003

cis
‐ and
trans
‐1,2‐divinylcyclobutane

product:
trans
‐1,2‐divinylcyclobutane
1‐(2‐Methoxycarbonylphenyl)Pyrrole
Authors: Josey A. D.
Published: November 2003

1‐(2‐Methoxycarbonylphenyl)pyrrole

product: 1‐(2‐methoxycarbonylphenyl)pyrrole

product: 1‐(2‐carboxyphenyl)pyrrole

product: 9‐keto‐9H‐pyrrole‐(1,2‐
a
)indole
2‐Methylcyclopentane‐1,3‐Dione
Authors: John Joseph P. , Swaminathan S. , Venkataramani P. S.
Published: November 2003

2‐Methylcyclopentane‐1,3‐dione

intermediate:2‐Methyl‐4‐ethoxalylcyclopentane‐1,3,5‐trione

intermediate:2‐Methylcyclopentane‐1,3,5‐trione hydrate

intermediate:2‐Methylcyclopentane‐1,3,5‐trione 5‐semicarbazone

product:2‐Methylcyclopentane‐1,3‐dione

byproduct: sodium sulfate
5‐Methyl‐5‐Hexen‐2‐One
Authors: Boatman Sandra , Hauser Charles R.
Published: November 2003

5‐Methyl‐5‐hexen‐2‐one

reactant: Eastman Organic Chemicals practical grade methallyl chloride

reactant: Union Carbide Chemicals Co. 2,4‐pentanedione

product: 5‐Methyl‐5‐hexen‐2‐one

product: 4‐Phenyl‐2‐butanone

product: 4‐(
o
‐Bromophenyl)‐2‐butanone

product: 4‐(
m
‐Bromophenyl)‐2‐butanone

product: 4‐(
o
‐Chlorophenyl)‐2‐butanone

product: 4‐(
m
‐Chlorophenyl)‐2‐butanone

product: 4‐(
p
‐Chlorophenyl)‐2‐butanone

product: 4‐(
m
‐Fluorophenyl)‐2‐butanone

product: 4‐(
m
‐Nitrophenyl)‐2‐butanone

product: 4‐(α‐Naphthyl)‐2‐butanone

product: 1‐Phenyl‐1,4‐pentanedione

product: 2‐Heptanone
Nicotinic Anhydride
Authors: Rinderknecht Heinrich , Gutenstein Morris
Published: November 2003

Nicotinic anhydride

intermediate: Triethylamine hydrochloride

product: nicotinic anhydride
Reduction of Organic Halides. Chlorobenzene to Benzene
Authors: Bryce‐Smith D. , Wakefield B. J.
Published: November 2003

Reduction of organic halides. chlorobenzene to benzene

product: benzene

product:
n
‐butane

product: 2‐methylbutane

product: isopropyl acetate

product: methane

product: naphthalene

product: styrene

product: aniline

product: phenol

product: acetone

product: cyclohexane

byproduct: cyclohexene

product: toluene
1‐
p
‐Tolylcyclopropanol
Authors: DePuy C. H. , Klein R. A.
Published: November 2003

1‐
p
‐Tolylcyclopropanol

product: 1‐
p
‐Tolylcyclopropanol
2‐(p‐Tolylsulfonyl)Dihydroisoindole
Authors: Bornstein J. , Shields J. E.
Published: November 2003

2‐(p‐Tolylsulfonyl)Dihydroisoindole

product: 2‐(p‐tolylsulfonyl)dihydroisoindole

solvent: Dimethylformamide, b.p. 152–154°, purchased from Matheson, Coleman and Bell

reactant:p‐toluenesulfonamide

reactant:o‐xylylene dibromide

product: N,N‐diethyl‐ and N,N‐di‐n‐butyl‐p‐toluenesulfonamide as well as 2‐(p‐tolylsulfonyl)benz[f]isoindoline
Aminomalononitrile
p
‐Toluenesulfonate
Authors: Ferris J. P. , Sanchez R. A. , Mancuso R. W.
Published: November 2003

Aminomalononitrile
p
‐toluenesulfonate

reactant: Malononitrile (25 g., 0.38 mole)

product: aminomalononitrile
p
‐toluenesulfonate
1‐Amino‐1‐Methylcyclohexane
Authors: Kovacic Peter , Chaudhary Sohan S.
Published: November 2003

1‐Amino‐1‐methylcyclohexane

product: 1‐amino‐1‐methylcyclohexane
cis
‐2‐Benzyl‐3‐Phenylaziridine
Authors: Kotera Katsumi , Kitahonoki Keizo
Published: November 2003

cis
‐2‐Benzyl‐3‐phenylaziridine

solvent: 100 ml. of petroleum ether

solvent: ether‐petroleum ether

product: 2‐benzyl‐3‐phenylaziridine

product: 2‐Phenylaziridine

product: 2‐Phenylaziridine

product: 2‐(α‐Naphthyl)‐aziridine

product: 2‐(α‐Methylbenzyl)‐aziridine

product: 2‐Phenyl‐aziridine

product: 2‐(α‐Naphthyl)‐aziridine

product: 2‐(α‐Methylbenzyl)‐aziridine
1,1′‐Carbonyldiimidazole
Authors: Staab Heinz A. , Wendel Kurt
Published: November 2003

1,1′‐Carbonyldiimidazole

product: 1,1′‐carbonyldiimidazole

reactant: Technical grade imidazole (from Badishe Anilin‐ und Soda‐Fabrik, Ludwigshafen, Rhein, Germany)
Chlorodiisopropylphosphine
Authors: Voskuil W. , Arens J. F.
Published: November 2003

Chlorodiisopropylphosphine

product: Chlorodiisopropylphosphine

product: chlorodiisobutylphosphine

product: chlorodi‐
sec
‐butylphosphine

product: chlorodi‐
t
‐butylphosphine

product: chlorodicyclohexylphosphine

product: dichloro‐
t
‐butylphosphine
Cinnamyl Bromide
Authors: Schaefer John P. , Higgins J. G. , Shenoy P. K.
Published: November 2003

Cinnamyl bromide

product: cinnamyl bromide
1,1‐Diphenylpentane
Authors: Murphy William S. , Hamrick Phillip J. , Hauser Charles R.
Published: November 2003

1,1‐Diphenylpentane

product: 1,1‐diphenylpentane
3‐Hydroxypyrene
Authors: Gumprecht W. H.
Published: November 2003

3‐Hydroxypyrene

reactant: 14.0 g. (0.050 mole) of 3‐bromopyrene

product: 3‐hydroxypyrene

reactant: pyrene
2‐Methylmercapto‐N‐Methyl‐Δ
2
‐Pyrroline
Authors: Gompper R. , Elser W.
Published: November 2003

2‐Methylmercapto‐N‐methyl‐Δ
2
‐pyrroline

intermediate:
N‐Methyl‐2‐pyrrolidinethione

intermediate:
2‐Methylmercapto‐N‐methyl
‐Δ
1
‐
pyrrolinium iodide

product:
2‐Methylmercapto‐N‐methyl
‐Δ
2
‐
pyrroline
.
(+)‐ and (−)‐α‐(2,4,5,7‐Tetranitro‐9‐fluorenylideneaminooxy)propionic Acid
Authors: Block Paul , Newman Melvin S.
Published: November 2003

(+)‐ and (−)‐α‐(2,4,5,7‐tetranitro‐9‐fluorenylideneaminooxy)propionic acid

intermediate: ethyl α‐(isopropylideneaminooxy)propionate

intermediate:
d,l‐α‐(Isopropylideneaminooxy)propionic acid

solvent: 160 ml. of petroleum ether

intermediate: (+)‐ and (−)‐
α‐(Isopropylideneaminooxy)propionic acid‐(−)‐ephedrine salts

intermediate: (−)‐ephedrine‐(−)‐α‐(isopropylideneaminooxy)propionic acid

intermediate: (+)‐α‐(isopropylideneaminooxy)propionic acid

intermediate: (−)‐base‐(−)‐acid salt

product: (+)‐
and (−)‐α‐(2,4,5,7‐Tetranitro‐9‐fluorenylideneaminooxy)propionic acid (TAPA)
p
‐Chlorophenoxymethyl Chloride
Authors: Gross H. , Bürger W.
Published: November 2003

p
‐Chlorophenoxymethyl chloride

byproduct: phosphorus trichloride

product:
p
‐chlorophenoxymethyl chloride

product: 2,4‐dichlorophenoxymethyl chloride
Diphenyl‐
p
‐Bromophenylphosphine
Authors: Schiemenz G. P.
Published: November 2003

Diphenyl‐
p
‐bromophenylphosphine

reactant: 15 ml. of a solution of 88.5 g. (0.38 mole) of
p
‐dibromobenzene

product: diphenyl‐
m
‐bromophenyl‐

product: diphenyl‐
p
‐chlorophenylphosphine

product: diphenyl‐
p
‐bromophenylphosphine
Methyl Ketones from Carboxylic Acids: Cyclohexyl Methyl Ketone
Authors: Bare Thomas M. , House Herbert O.
Published: November 2003

Methyl ketones from carboxylic acids: cyclohexyl methyl ketone

solvent: Commercial 1,2‐dimethoxyethane, b.p. 85–86°, purchased from Eastman Organic Chemicals, was distilled from lithium aluminum hydride before use

reactant: cyclohexanecarboxylic acid, m.p. 31–32°, purchased from Aldrich Chemical Company was used without further purification

product: cyclohexyl methyl ketone
exo/endo
‐7‐Norcaranol
Authors: Schöllkopf U. , Paust J. , Patsch M. R.
Published: November 2003

exo/endo
‐7‐norcaranol

reactant: 49.0 g. (0.300 mole) of dichloromethyl 2‐chloroethyl ether

intermediate:
exo/endo
‐7‐(2‐chloroethoxy)bicyclo[4.1.0]heptane

product:
exo/endo
‐7‐norcaranol

reactant: 2‐Ethoxy‐1,3‐dioxolane

intermediate: 2‐chloroethyl formate

byproduct: Isopropyl 2‐chloroethyl ether

product:
exo
‐7‐norcaranol
Tetracyanoethylene Oxide
Authors: Linn W. J.
Published: November 2003

Tetracyanoethylene oxide

product: tetracyanoethylene oxide
2,4,6‐Triphenylnitrobenzene
Authors: Dimroth K. , Berndt A. , Reichardt C.
Published: November 2003

2,4,6‐Triphenylnitrobenzene

reactant: 21 ml. (24 g., 0.39 mole) of nitromethane

solvent: Triethylamine (70 ml., 51 g.)

product: 2,4,6‐triphenylnitrobenzene
2,4,6‐Trimethylpyrylium Tetrafluoroborate
Authors: Balaban A. T. , Boulton A. J.
Published: November 2003

2,4,6‐Trimethylpyrylium tetrafluoroborate

product: 2,4,6‐Trimethylpyrylium tetrafluoroborate
Acetic Formic Anhydride
Authors: Krimen Lewis I.
Published: November 2003

Acetic formic anhydride

product: acetic formic anhydride
cis
‐4‐
tert
‐Butylcyclohexanol
Authors: Eliel E. L. , Doyle T. W. , Hutchins R. O. , Gilbert E. C.
Published: November 2003

cis
‐4‐
tert
‐Butylcyclohexanol

product:
cis
‐4‐
tert
‐butylcyclohexanol
trans,trans
‐1,3‐Butadiene‐1,4‐diyl Diacetate
Authors: Carlson Robert M. , Hill Richard K.
Published: November 2003

trans,trans
‐1,3‐Butadiene‐1,4‐diyl diacetate

intermediate:
trans
‐7,8‐diacetoxybicyclo[4.2.0]octa‐2,4‐diene

solvent: petroleum ether

product:
trans,trans
‐1,3‐butadiene‐1,4‐diyl diacetate
cis
‐3,4‐Dichlorocyclobutene
Authors: Pettit R. , Henery J.
Published: November 2003

cis
‐3,4‐Dichlorocyclobutene

byproduct: 1,4‐dichlorobutadiene

product:
cis
‐3,4‐dichlorocyclobutene
Diethyl
tert
‐Butylmalonate
Authors: Eliel E. L. , Hutchins R. O. , Knoeber M.
Published: November 2003

Diethyl
tert
‐butylmalonate

reactant: 400 g. (2.50 moles) of diethyl malonate

intermediate: diethyl isopropylidenemalonate

product: diethyl
tert
‐butylmalonate
2,2‐Dimethyl‐4‐Phenylbutyric Acid
Authors: Creger P. L.
Published: November 2003

2,2‐Dimethyl‐4‐phenylbutyric acid

reactant: 7.75 g. (0.0767 mole) of diisopropylamine

product: 2,2‐dimethyl‐4‐phenylbutyric acid
2,3‐Diphenyl‐1,3‐butadiene
Authors: Iwai Issei , Ide Junya
Published: November 2003

2,3‐Diphenyl‐1,3‐butadiene

reactant: 30 ml. of anhydrous dimethyl sulfoxide

product: 2,3‐diphenyl‐1,3‐butadiene
2,3‐Diphenylvinylene Sulfone
Authors: Carpino Louis A. , McAdams Louis V.
Published: November 2003

2,3‐Diphenylvinylene sulfone

reactant: 6.36 g. (0.0157 mole) of crude α,α′‐dibromodibenzyl sulfone

product: vinylene sulfone
Directed Aldol Condensations: β‐Phenylcinnamaldehyde
Authors: Wittig G. , Hesse A.
Published: November 2003

Directed aldol condensations: β‐phenylcinnamaldehyde

reactant: 99.2 g. (1.00 mole) of freshly distilled cyclohexylamine

reactant: 44.1 g. (1.00 mole) of freshly distilled acetaldehyde

intermediate:
N
‐ethylidenecyclohexylamine

solvent: 2.53 g. (3.60 ml. or 0.0250 mole) of pure diisopropylamine

intermediate:
N
‐(3‐hydroxy‐3,3‐diphenylpropylidene)cyclohexylamine

product: β‐phenylcinnamaldehyde
p
‐Acetyl‐α‐Bromohydrocinnamic Acid
Authors: Cleland George H.
Published: November 2003

p
‐acetyl‐α‐bromohydrocinnamic acid

product:
p
‐acetyl‐α‐bromohydrocinnamic acid
Bicyclo[3.2.1]octan‐3‐one
Authors: Jefford C. W. , Gunsher J. , Hill D. T. , Brun P. , Le Gras J. , Waegell B.
Published: November 2003

Bicyclo[3.2.1]octan‐3‐one

solvent: 400 ml. of petroleum ether

intermediate:
exo
‐3,4‐dichlorobicyclo[3.2.1]oct‐2‐ene

intermediate: 3‐chlorobicyclo[3.2.1]oct‐2‐ene

product: bicyclo[3.2.1]octan‐3‐one