bluuebunny/crossref_metadata_2025 huggingface dataset:
p
‐Nitrophenylarsonic Acid
Authors: Ruddy A. Wayne , Starkey Edgar B.
Published: November 2003

p
‐nitrophenylarsonic acid

product:
p
‐nitrophenylarsonic acid

product: phenyl

product:
o
‐nitrophenyl

product:
m
‐nitrophenyl

product:
o
‐tolyl

product:
m
‐tolyl

product:
p
‐tolyl

product:
o
‐chlorophenyl

product:
p
‐chlorophenyl

product:
o
‐carboxyphenyl

product:
p
‐carboxyphenyl

product:
p
‐carbethoxyphenyl

product:
p
‐acetophenyl
Palladium Catalysts
Authors: Mozingo Ralph
Published: November 2003

Palladium catalysts

product: Palladium on barium sulfate catalyst (5% Pd)

product: Palladium on carbon catalyst (5% Pd)

product: Palladium chloride on carbon (5% Pd)

product: Palladium on carbon catalyst (10% Pd)
Pyocyanine
Authors: Surrey Alexander R.
Published: November 2003

Pyocyanine

intermediate: α‐
Methoxyphenazine

reactant: 6 g. (0.06 mole) of
o
‐phenylenediamine

intermediate: α‐
Hydroxyphenazine

product:
Pyocyanine
o
‐Tolualdehyde
Authors: Williams Jonathan W. , Witten Charles H. , Krynitsky John A.
Published: November 2003

o
‐Tolualdehyde

product:
o
‐tolualdehyde
tert
‐Butylamine
Authors: Campbell Kenneth N. , Sommers Armiger H. , Campbell Barbara K. , Smith Lee Irvin , Emerson Oliver H. , Pearson D. E. , Baxter J. F. , Carter K. N.
Published: November 2003

tert
‐Butylamine

intermediate: 2,2‐Dimethylethylenimine

product:
tert
‐butylamine

intermediate:
tert
‐butylurea

solvent: 500 ml. of petroleum ether

intermediate:
tert
‐butylphthalimide

intermediate:
tert
‐butylamine hydrochloride

reactant:
tert
‐butyl alcohol

byproduct: di‐
tert
‐butylurea

intermediate:
tert
‐amylurea

intermediate:
tert
‐amylphthalimide

product:
tert
‐amylamine
Carboxymethoxylamine Hemihydrochloride
Authors: Anker H. S. , Clarke H. T.
Published: November 2003

Carboxymethoxylamine hemihydrochloride

intermediate: acetone carboxymethoxime

product: Carboxymethoxylamine hemihydrochloride
Decamethylenediamine
Authors: Biggs B. S. , Bishop W. S.
Published: November 2003

Decamethylenediamine

product: decamethylenediamine
Ethyl α‐Isopropylacetoacetate
Authors: Adams Joe T. , Levine Robert , Hauser Charles R.
Published: November 2003

Ethyl α‐isopropylacetoacetate

product: ethyl α‐cyclohexylacetoacetate

product: ethyl α‐
tert
‐butylacetoacetate

product: Ethyl α‐isopropylacetoacetate
Glycolonitrile
Authors: Gaudry Roger
Published: November 2003

Glycolonitrile

product: glycolonitrile
1‐Methyl‐2‐imino‐β‐naphthothiazoline
Authors: Cressman Homer W. J.
Published: November 2003

1‐Methyl‐2‐imino‐β‐naphthothiazoline

product: 1‐methyl‐2‐imino‐β‐naphthothiazoline

solvent: petroleum ether

product: 2‐imino‐1‐methylnaphtho [1,2] selenazoline

product: 2‐imino‐1‐ethylnaphtho [1,2] selenazoline
N‐Methyl‐1‐Naphthylcyanamide
Authors: Cressman Homer W. J.
Published: November 2003

N‐methyl‐1‐naphthylcyanamide

: N‐ethyl‐1‐naphthylcyanamide

intermediate: 10 g. of α‐naphthyltrimethylammonium bromide

product: N‐methyl‐1‐naphthylcyanamide
3‐Penten‐2‐Ol
Authors: Coburn E. R.
Published: November 2003

3‐Penten‐2‐ol

product: 3‐penten‐2‐ol
γ‐
n
‐Propylbutyrolactone and β‐(Tetrahydrofuryl)Propionic Acid
Authors: Schwenk Erwin , Papa Domenick , Hankin Hilda , Ginsberg Helen
Published: November 2003

γ‐
n
‐propylbutyrolactone and β‐(tetrahydrofuryl)propionic acid

product: γ‐
n
‐propylbutyrolactone

product: β‐(tetrahydrofuryl) propionic acid

product: ω‐hydroxycaprylic acid

product: δ‐
n
‐propylvalerolactone
Pseudothiohydantoin
Authors: Allen C. F. H. , VanAllan J. A.
Published: November 2003

Pseudothiohydantoin

reactant: 76 g. (1 mole) of thiourea

product: pseudothiohydantoin

intermediate: hydrochloride
o
‐Toluic Acid
Authors: Zaugg Harold E. , Rapala Richard T.
Published: November 2003

o
‐Toluic acid

product:
o
‐Toluic acid
1,3,5‐Triacetylbenzene
Authors: Frank Robert L. , Varland Robert H.
Published: November 2003

1,3,5‐Triacetylbenzene

product: triacetylbenzene
2‐Allylcyclohexanone
Authors: Vanderwerf Calvin A. , Lemmerman Leo V.
Published: November 2003

2‐Allylcyclohexanone

reactant: Cyclohexanone (220 g., 2.24 moles)

reactant: 246 g. (2.03 moles) of allyl bromide

product: 2‐allylcyclohexanone

byproduct: diallylcyclohexanone
9‐Bromophenanthrene
Authors: Dornfeld Clinton A. , Callen Joseph E. , Coleman George H.
Published: November 2003

9‐Bromophenanthrene

reactant: One and one‐half kilograms of technical 90% phenanthrene

product: 9‐bromophenanthrene
trans
‐1,2‐Cyclohexanediol
Authors: Roebuck Alan , Adkins Homer
Published: November 2003

trans
‐1,2‐Cyclohexanediol

product:
trans
‐1,2‐Cyclohexanediol
Ethyl Azodicarboxylate
Authors: Rabjohn Norman
Published: November 2003

Ethyl azodicarboxylate

intermediate: ethyl hydrazodicarboxylate

product: ethyl azodicarboxylate
Fluorenone‐2‐Carboxylic Acid
Authors: Rieveschl George , Ray F. E.
Published: November 2003

Fluorenone‐2‐carboxylic acid

reactant: 50 g. (0.24 mole) of 2‐acetylfluorene

product: fluorenone‐2‐carboxylic acid
Hexamethylene Chlorohydrin
Authors: Campbell Kenneth N. , Sommers Armiger H.
Published: November 2003

Hexamethylene chlorohydrin

intermediate: hexamethylene dichloride

product: hexamethylene chlorohydrin
dl‐Isopropylideneglycerol
Authors: Renoll Mary , Newman Melvin S.
Published: November 2003

dl‐Isopropylideneglycerol

solvent: 300 ml. of low‐boiling petroleum ether

product: isopropylideneglycerol
1‐Phenyl‐3‐amino‐5‐pyrazolone
Authors: Porter H. D. , Weissberger A.
Published: November 2003

1‐Phenyl‐3‐amino‐5‐pyrazolone

product: 1‐phenyl‐3‐amino‐5‐pyrazolone
m
‐Aminobenzaldehyde Dimethylacetal
Authors: Icke Roland N. , Redemann C. Ernst , Wisegarver Burnett B. , Alles Gordon A.
Published: November 2003

m
‐aminobenzaldehyde dimethylacetal

product:
m
‐aminobenzaldehyde dimethylacetal
Catalyst,
R
aney Nickel,
W
‐6
Authors: Billica Harry R. , Adkins Homer
Published: November 2003

Catalyst, Raney nickel, W‐6

product:
W
‐6
Raney nickel
α,α‐Diphenylacetone
Authors: Schultz Everett M. , Mickey Sally
Published: November 2003

α,α‐Diphenylacetone

product: α,α‐diphenylacetone
Homophthalic Acid and Anhydride
Authors: Grummitt Oliver , Egan Richard , Buck Allen
Published: November 2003

Homophthalic acid and anhydride

product: homophthalic acid

product: Homophthalic anhydride
β‐(2‐Hydroxyethylmercapto)propionitrile
Authors: Gershbein Leon L.
Published: November 2003

β‐(2‐Hydroxyethylmercapto)propionitrile

product: β‐(2‐hydroxyethylmercapto) propionitrile
Indazole
Authors: Stephenson Emily F. M.
Published: November 2003

Indazole

intermediate:
o
‐hydrazinobenzoic acid hydrochloride

intermediate: indazolone

intermediate: 3‐chloroindazole

product: indazole

solvent: 25 ml. of petroleum ether

intermediate:
o
‐Hydrazinobenzoic acid
Isoprene Cyclic Sulfone
Authors: Frank Robert L. , Seven Raymond P.
Published: November 2003

Isoprene cyclic sulfone

product: butadiene

product: 2,3‐dimethylbutadiene

product: Isoprene cyclic sulfone
Methacrylamide
Authors: Wiley Richard H. , Waddey Walter E.
Published: November 2003

Methacrylamide

product: methacrylamide
5‐Nitro‐2,3‐Dihydro‐1,4‐Phthalazinedione
Authors: Redemann Carl T. , Redemann C. Ernst
Published: November 2003

5‐Nitro‐2,3‐dihydro‐1,4‐phthalazinedione

product: 5‐nitro‐2,3‐dihydro‐1,4‐phthalazinedione
Oleyl Alcohol
Authors: Adkins Homer , Gillespie R. H.
Published: November 2003

Oleyl alcohol

reactant: 200 g. (230 ml., 0.65 mole) of ethyl oleate

reactant: 1.5 l. of absolute ethanol

product: oleyl alcohol
Trimethylene Oxide
Authors: Noller C. R.
Published: November 2003

Trimethylene oxide

product: trimethylene oxide
DL‐Aspartic Acid
Authors: Dunn M. S. , Smart B. W.
Published: November 2003

DL‐Aspartic acid

reactant: 735 g. (6.0 moles) of ethyl chloroacetate

intermediate: triethyl α‐phthalimidoethane‐α,α,β‐tricarboxylate

byproduct: phthalic acid

product:DL‐aspartic acid

reactant: 490 to 536 g. of ethyl chloroacetate

byproduct: glycine
β‐Carbethoxy‐γ,γ‐Diphenylvinylacetic Acid
Authors: Johnson William S. , Schneider William P.
Published: November 2003

β‐carbethoxy‐γ,γ‐diphenylvinylacetic acid

solvent: petroleum ether

product: β‐Carbethoxy‐γ,γ‐diphenylvinylacetic acid
Chloroacetonitrile
Authors: Reisner D. B. , Horning E. C.
Published: November 2003

Chloroacetonitrile

solvent: 800 ml. of dry technical trimethylbenzene

product: chloroacetonitrile
trans
‐2‐Chlorocyclopentanol
Authors: Donahoe Hugh B. , Vanderwerf Calvin A.
Published: November 2003

trans
‐2‐Chlorocyclopentanol

product:
trans
‐2‐chlorocyclopentanol
1,4‐Diiodobutane
Authors: Stone Herman , Shechter Harold
Published: November 2003

1,4‐Diiodobutane

product: 1,4‐diiodobutane
5‐Ethyl‐2‐methylpyridine
Authors: Frank Robert L. , Pilgrim Frederick J. , Riener Edward F.
Published: November 2003

5‐Ethyl‐2‐methylpyridine

byproduct: α‐picoline

product: 5‐ethyl‐2‐methylpyridine
Ethyl Phenylcyanoacetate
Authors: Horning E. C. , Finelli A. F.
Published: November 2003

Ethyl phenylcyanoacetate

product: Ethyl Phenylcyanoacetate
Hexahydro‐1,3,5‐tripropionyl‐
s
‐triazine
Authors: Teeters W. O. , Gradsten M. A.
Published: November 2003

Hexahydro‐1,3,5‐tripropionyl‐
s
‐triazine

product: hexahydro‐1,3,5‐tripropionyl‐
s
‐triazine
Methyl β‐Thiodipropionate
Authors: Fehnel Edward A. , Carmack Marvin
Published: November 2003

Methyl β‐thiodipropionate

product: Methyl β‐thiodipropionate

reactant: commercial methyl acrylate
o
‐Nitroacetophenone
Authors: Reynolds George A. , Hauser Charles R.
Published: November 2003

o
‐Nitroacetophenone

product:
o
‐nitroacetophenone

product:
p
‐nitroacetophenone

product:
o
‐chloroacetophenone
α‐Phenyl‐α‐Carbethoxyglutaronitrile
Authors: Horning E. C. , Finelli A. F.
Published: November 2003

α‐phenyl‐α‐carbethoxyglutaronitrile

product: α‐Phenyl‐α‐carbethoxyglutaronitrile
Phenylsuccinic Acid
Authors: Allen C. F. H. , Johnson H. B.
Published: November 2003

Phenylsuccinic acid

intermediate: ethyl β‐phenyl‐β‐cyanopropionate

product: phenylsuccinic acid
1,2,3,4‐Tetrahydrocarbazole
Authors: Rogers Crosby U. , Corson B. B.
Published: November 2003

1,2,3,4‐Tetrahydrocarbazole

product: 1,2,3,4‐tetrahydrocarbazole
Vinyl Laurate and Other Vinyl Esters
Authors: Swern Daniel , Jordan E. F.
Published: November 2003

Vinyl laurate and other vinyl esters

reactant: 206 g. (2.4 moles) of freshly distilled vinyl acetate

reactant: 80 g. (0.4 mole) of lauric acid

product: vinyl laurate

product: Caproate

product: Caprylate

product: Pelargonate

product: Caprate

product: Myristate

product: Palmitate (m.p. 26.7–27.1°)

product: Stearate (m.p. 35–36°)

product: 10‐Hendecenoate

product: Oleate

reactant: caproic acid, b.p. 96°/8 mm., Carbide and Carbon Chemicals Corporation, New York

reactant: caprylic acid

reactant: capric acid, b.p. 145–146°/8 mm., Armour and Company, Chicago, Illinois

reactant: pelargonic acid, b.p. 176°/64 mm., Emery Industries, Cincinnati, Ohio

reactant: 10‐hendecenoic (undecylenic) acid, b.p. 177–180°/25 mm., Baker Castor Oil Company, New York
Arylureas:
p
‐Ethoxyphenylurea
Authors: Kurzer Frederick
Published: November 2003

Arylureas:
p
‐ethoxyphenylurea

product:
p
‐ethoxyphenylurea

product:
p
‐methoxyphenylurea

product: 1‐(2‐hydroxy‐1‐naphthyl)urea
Ethyl α‐Acetyl‐β‐(2,3‐Dimethoxyphenyl)‐Propionate
Authors: Horning E. C. , Koo J. , Fish M. S. , Walker G. N.
Published: November 2003

Ethyl α‐acetyl‐β‐(2,3‐dimethoxyphenyl)‐propionate

intermediate:
Ethyl α‐acetyl‐β‐(2,3‐dimethoxyphenyl)acrylate.

product:
Ethyl α‐acetyl‐β‐(2,3‐dimethoxyphenyl)propionate.

catalyst: 5 g. of 5% palladium‐on‐carbon
Ethyl Pyruvate
Authors: Cornforth J. W.
Published: November 2003

Ethyl pyruvate

solvent: 500 ml. of light petroleum ether

reactant: 50 g. (0.42 mole) of ethyl lactate

product: ethyl pyruvate
Iodocyclohexane
Authors: Stone Herman , Shechter Harold
Published: November 2003

Iodocyclohexane

product: iodocyclohexane
Methyl Cyclopropyl Ketone
Authors: Cannon George W. , Ellis Ray C. , Leal Joseph R.
Published: November 2003

Methyl cyclopropyl ketone

intermediate: 5‐chloro‐2‐pentanone

product: methyl cyclopropyl ketone

intermediate: ether‐ketone
9‐Nitroanthracene
Authors: Braun Charles E. , Cook Clinton D. , Merritt Charles , Rousseau Joseph E.
Published: November 2003

9‐Nitroanthracene

reactant: Twenty grams (0.112 mole) of finely powdered anthracene

product: 9‐nitroanthracene
1‐(
p
‐Nitrophenyl)‐1,3‐Butadiene
Authors: Ropp Gus A. , Coyner Eugene C.
Published: November 2003

1‐(
p
‐Nitrophenyl)‐1,3‐butadiene

reactant: 138 g. (1.0 mole) of
p
‐nitroaniline

intermediate: 1‐(
p
‐nitrophenyl)‐4‐chloro‐2‐butene

solvent: 500 ml. of ligroin

product: 1‐(
p
‐nitrophenyl)‐1,3‐butadiene
γ‐Phenylallylsuccinic Acid
Authors: Rondestvedt Christian S.
Published: November 2003

γ‐Phenylallylsuccinic acid

product: γ‐Phenylallylsuccinic acid

intermediate: γ‐Phenylallylsuccinic anhydride
Syringic Aldehyde
Authors: Allen C. F. H. , Leubner Gerhard W.
Published: November 2003

Syringic Aldehyde

product: syringic aldehyde
Tetraphenylethylene
Authors: Buckles Robert E. , Matlack George M.
Published: November 2003

Tetraphenylethylene

reactant: 75 g. (0.32 mole) of diphenyldichloromethane

product: tetraphenylethylene
2‐Thenaldehyde
Authors: Weston Arthur W. , Michaels R. J.
Published: November 2003

2‐Thenaldehyde

byproduct: N‐methylaniline

product: 2‐thenaldehyde
Acrolein Acetal
Authors: VanAllan J. A.
Published: November 2003

Acrolein acetal

product: acrolein acetal

product: crotonaldehyde diethyl acetal

product: Tiglylaldehyde diethyl acetal
Alloxan Monohydrate
Authors: Holmgren A. V. , Wenner Wilhelm
Published: November 2003

Alloxan monohydrate

product: alloxan monohydrate
β‐Bromoethylphthalimide
Authors: Soine T. O. , Buchdahl M. R.
Published: November 2003

β‐bromoethylphthalimide

product: β‐bromoethylphthalimide

intermediate: β‐hydroxyethylphthalimide
3‐Cyano‐6‐Methyl‐2(1)‐Pyridone
Authors: Mariella Raymond P.
Published: November 2003

3‐Cyano‐6‐methyl‐2(1)‐pyridone

product: 3‐cyano‐6‐methyl‐2(1)‐pyridone
Cyclopentadiene and 3‐Chlorocyclopentene
Authors: Moffett Robert Bruce
Published: November 2003

Cyclopentadiene and 3‐chlorocyclopentene

product: cyclopentadiene

product:
3‐Chlorocyclopentene
2,2‐Dichloroethanol
Authors: Sroog C. E. , Woodburn H. M.
Published: November 2003

2,2‐Dichloroethanol

product: 2,2‐dichloroethanol
1,1′‐Dicyano‐1,1′‐Bicyclohexyl
Authors: Overberger C. G. , Berenbaum M. B.
Published: November 2003

1,1′‐dicyano‐1,1′‐bicyclohexyl

product: Tetramethylsuccinonitrile

solvent: petroleum ether

product: 1,1′‐Dicyano‐1,1′‐bicyclohexyl
asym
‐Dimethylurea
Authors: Kurzer Frederick
Published: November 2003

asym
‐Dimethylurea

product:
asym
‐dimethylurea
Ethyl Orthocarbonate
Authors: Roberts John D. , McMahon Robert E.
Published: November 2003

Ethyl orthocarbonate

product: ethyl orthocarbonate
1,1′‐Ethynylene‐
bis
‐Cyclohexanol
Authors: Woods G. Forrest , Schwartzman Louis H.
Published: November 2003

1,1′‐Ethynylene‐
bis
‐cyclohexanol

product: 1,1′‐ethynylene‐
bis
‐cyclohexanol
Isodehydroacetic Acid and Ethyl Isodehydroacetate
Authors: Smith Newton R. , Wiley Richard H.
Published: November 2003

Isodehydroacetic acid and ethyl isodehydroacetate

product: isodehydroacetic acid

product: ethyl isodehydroacetate
β‐Ketoisoöctaldehyde Dimethyl Acetal
Authors: Price Charles C. , Pappalardo Joseph A.
Published: November 2003

β‐Ketoisoöctaldehyde dimethyl acetal

product: β‐ketoisoöctaldehyde dimethyl acetal
Methyl γ‐Methyl‐γ‐nitrovalerate
Authors: Moffett R. B.
Published: November 2003

Methyl γ‐methyl‐γ‐nitrovalerate

product: Methyl γ‐methyl‐γ‐nitrovalerate
Thiobenzoic Acid
Authors: Noble Paul , Tarbell D. S.
Published: November 2003

Thiobenzoic acid

product: thiobenzoic acid
3‐Acetamido‐2‐butanone
Authors: Wiley Richard H. , Borum O. H.
Published: November 2003

3‐Acetamido‐2‐butanone

product: 3‐acetamido‐2‐butanone

product: 1‐phenyl‐1‐propionamido‐2‐butanone

product: acetamidoacetylacetone

product: N‐methylacetamidoacetone

product: 1‐phenyl‐2‐acetamido‐3‐butanone

product: 1‐phenyl‐2‐propionamido‐3‐pentanone

product: 1‐phenyl‐2‐butyramido‐3‐hexanone

product: α‐benzamidopropiophenone

product: α‐benzamido‐β‐phenylpropiophenone

product: 1‐phenyl‐1‐acetamidoacetone

product: 1‐phenyl‐1‐benzamidoacetone

product: 1‐phenyl‐2‐benzamido‐3‐butanone

product: 3‐benzamido‐2‐butanone

product: 3‐acetamido‐5‐methyl‐2‐hexanone
Alloxantin Dihydrate
Authors: Tipson R. Stuart
Published: November 2003

Alloxantin dihydrate

product: alloxantin dihydrate
Atrolactic Acid
Authors: Eliel Ernest L. , Freeman Jeremiah P.
Published: November 2003

Atrolactic acid

product: atrolactic acid

solvent: 25 ml. of commercial pentane

product: atrolactic acid hemihydrate

reactant: Acetophenone (15–16.5 g., b.p. 92–94°/20 mm.)
Benzhydryl β‐Chloroethyl Ether
Authors: Sugasawa Shigehiko , Fujiwara Kunio
Published: November 2003

Benzhydryl β‐chloroethyl ether

reactant: 36 g. (0.45 mole) of ethylene chlorohydrin

reactant: 55 g. (0.30 mole) of benzhydrol

product: benzhydryl β‐chloroethyl ether
Butyrchloral
Authors: Ropp Gus A. , Craig W. E. , Raaen Vernon
Published: November 2003

Butyrchloral

product: butyrchloral

intermediate: α‐chlorocrotonaldehyde
p
‐Dimethylaminobenzaldehyde
Authors: Campaigne E. , Archer W. L.
Published: November 2003

p
‐Dimethylaminobenzaldehyde

product:
p
‐Dimethylaminobenzaldehyde
Dimethylketene
Authors: Smith C. W. , Norton D. G.
Published: November 2003

Dimethylketene

intermediate: α‐bromoisobutyryl bromide

product: Dimethylketene

product: Isobutyroanilide
9‐Fluorenecarboxylic Acid
Authors: Richter Henry J.
Published: November 2003

9‐Fluorenecarboxylic acid

reactant: 45.6 g. (0.2 mole) of benzilic acid

product: 9‐fluorenecarboxylic acid

solvent: 40 ml. of petroleum ether
1,4‐Naphthoquinone
Authors: Braude E. A. , Fawcett J. S.
Published: November 2003

1,4‐Naphthoquinone

product: 1,4‐naphthoquinone

solvent: 500 ml. of petroleum ether

solvent: Skellysolve C
Nicotinonitrile
Authors: Teague Peyton C. , Short William A.
Published: November 2003

Nicotinonitrile

product: nicotinonitrile
m
‐Nitrobiphenyl
Authors: Kaslow C. E. , Summers R. M.
Published: November 2003

m
‐Nitrobiphenyl

reactant: 276 g. (2 moles) of technical grade m‐nitroaniline

intermediate: 1‐(
m
‐nitrophenyl)‐3,3‐dimethyltriazene

product:
m
‐nitrobiphenyl
6‐Nitroveratraldehyde
Authors: Fetscher Charles A.
Published: November 2003

6‐Nitroveratraldehyde

reactant: Veratraldehyde,Org. Syntheses Coll. Vol. 2, 619 (1943). 70 g. (0.42 mole)

product: 6‐nitroveratraldehyde

byproduct: 6‐nitrosoveratric acid
4‐Pentyn‐1‐ol
Authors: Jones E. R. H. , Eglinton Geoffrey , Whiting M. C.
Published: November 2003

4‐Pentyn‐1‐ol

product: 4‐pentyn‐1‐ol

product: α‐naphthylurethan of 4‐pentyn‐1‐ol
o
‐Phenylene Carbonate
Authors: Hanslick R. S. , Bruce W. F. , Mascitti A.
Published: November 2003

o
‐phenylene carbonate

product:
o
‐phenylene carbonate
3‐Thenaldehyde
Authors: Campaigne E. , Bourgeois R. C. , McCarthy W. C.
Published: November 2003

3‐Thenaldehyde

product: 3‐Thenaldehyde
3‐Thenyl Bromide
Authors: Campaigne E. , Tullar B. F.
Published: November 2003

3‐Thenyl bromide

product: 3‐thenyl bromide
2‐
p
‐Acetylphenylhydroquinone
Authors: Reynolds George A. , VanAllan J. A.
Published: November 2003

2‐
p
‐Acetylphenylhydroquinone

product: 2‐
p
‐acetylphenylquinone

product: 2‐
p
‐acetylphenylhydroquinone diacetate
β‐(
o
‐Carboxyphenyl)Propionic Acid
Authors: Page G. A. , Tarbell D. S.
Published: November 2003

β‐(
o
‐carboxyphenyl)propionic acid

intermediate:
o
‐carboxycinnamic acid

product: β‐(
o
‐carboxyphenyl)propionic acid

product: lactone of β‐hydroxy‐β‐(
o
‐carboxyphenyl)propionic acid (phthalideacetic acid)
Di‐
tert
‐butyl Malonate
Authors: McCloskey Allen L. , Fonken Gunther S. , Kluiber Rudolph W. , Johnson William S. , Raha Chittaranjan
Published: November 2003

Di‐
tert
‐butyl malonate

product: di‐
tert
‐butyl malonate

product:
tert
‐butyl acetate

product:
tert
‐butyl chloroacetate

product:
tert
‐butyl bromoacetate

product:
tert
‐butyl α‐chloropropionate

product:
tert
‐butyl
o
‐benzoylbenzoate

product: di‐
tert
‐butyl succinate

product: di‐
tert
‐butyl glutarate

product: di‐
tert
‐butyl β,β‐dimethylglutarate

intermediate: 28.0 g. (0.2 mole) of malonyl dichloride
p,p
′‐Dinitrobibenzyl
Authors: House Herbert O.
Published: November 2003

p,p′‐Dinitrobibenzyl

reactant: 100 g. (0.73 mole) of
p
‐nitrotoluene

product:
p,p
′‐dinitrobibenzyl
Ethoxyacetylene
Authors: Jones E. R. H. , Eglinton Geoffrey , Whiting M. C. , Shaw B. L.
Published: November 2003

Ethoxyacetylene

product: ethoxyacetylene

product: methoxyacetylene

solvent: 50‐ml. portions of high‐boiling petroleum
Ethyl Enanthylsuccinate
Authors: Patrick Tracy M. , Erickson Floyd B.
Published: November 2003

Ethyl enanthylsuccinate

reactant: 228 g. (2.0 moles) of enanthaldehyde

product: ethyl enanthylsuccinate

product: γ‐oxocapric acid

product: γ‐caprilactone
Methylisourea Hydrochloride
Authors: Kurzer Frederick , Lawson Alexander
Published: November 2003

Methylisourea hydrochloride

intermediate: cyanamide

product: methylisourea hydrochloride
3‐Methyl‐1,5‐pentanediol
Authors: Longley Raymond I. , Emerson William S.
Published: November 2003

3‐Methyl‐1,5‐pentanediol

product: 3‐methyl‐1,5‐pentanediol

byproduct: β‐methylglutaraldehyde
Phenanthrenequinone
Authors: Wendland Ray , LaLonde John
Published: November 2003

Phenanthrenequinone

reactant: 100 g. (0.56 mole) of phenanthrene

byproduct: anthraquinone

product: phenanthrenequinone
Tetralin Hydroperoxide
Authors: Knight H. B. , Swern Daniel
Published: November 2003

Tetralin hydroperoxide

reactant: 600 g. (4.54 moles) of pure tetralin

product: tetralin hydroperoxide
sec
‐Butyl α‐
n
‐Caproylpropionate
Authors: Rinehart Kenneth L.
Published: November 2003

sec
‐butyl α‐
n
‐caproylpropionate

reactant: 38.9 g. (0.40 mole) of
n
‐capronitrile

reactant: 125.4 g. (0.60 mole) of
sec
‐butyl α‐bromopropionate

product:
sec
‐butyl α‐
n
‐caproylpropionate

product: 5‐pyrazolone
2‐Butyn‐1‐ol
Authors: Ashworth P. J. , Mansfield G. H. , Whiting M. C.
Published: November 2003

2‐butyn‐1‐ol

intermediate: 3‐chloro‐2‐buten‐1‐ol

product: 2‐butyn‐1‐ol
α‐(4‐Chlorophenyl)‐γ‐Phenylacetoacetonitrile
Authors: Coan Stephen B. , Becker Ernest I.
Published: November 2003

α‐(4‐Chlorophenyl)‐γ‐phenylacetoacetonitrile

product: α‐(4‐chlorophenyl)‐γ‐phenylacetoacetonitrile

product: α‐Phenyl‐γ‐phenyl‐

product: α‐Phenyl‐γ‐(4‐methylphenyl)‐

product: α‐Phenyl‐γ‐(4‐methoxyphenyl)‐

product: α‐Phenyl‐γ‐(4‐bromophenyl)‐

product: α‐Phenyl‐γ‐(4‐methylthiophenyl)‐

product: α‐(4‐Fluorophenyl)‐γ‐phenyl‐
2‐Chloropyrimidine
Authors: Kogon Irving C. , Minin Ronald , Overberger C. G.
Published: November 2003

2‐Chloropyrimidine

product: 2‐chloropyrimidine
Ethyl Diethoxyacetate
Authors: Moffett Robert Bruce
Published: November 2003

Ethyl diethoxyacetate

product: ethyl diethoxyacetate
5‐Methylfurfuryldimethylamine
Authors: Eliel Ernest L. , Fisk Milton T.
Published: November 2003

5‐Methylfurfuryldimethylamine

product: 5‐methylfurfuryldimethylamine
4‐Methyl‐6‐Hydroxypyrimidine
Authors: Foster H. M. , Snyder H. R.
Published: November 2003

4‐Methyl‐6‐hydroxypyrimidine

intermediate: 2‐thio‐6‐methyluracil

product: 4‐methyl‐6‐hydroxypyrimidine
α‐Tetralone
Authors: Olson Cecil E. , Bader Alfred R. , Johnson G. Dana
Published: November 2003

α‐Tetralone

reactant: 104 g. (1.21 moles) of γ‐butyrolactone

product: α‐tetralone

: 4‐methyl‐1‐tetralone
N‐2‐Cyanoethylaniline
Authors: Cymerman‐Craig J. , Moyle M.
Published: November 2003

N‐2‐Cyanoethylaniline

product: N‐2‐cyanoethyl‐
p
‐anisidine

product: N‐2‐cyanoethyl‐
m
‐chloroaniline

product: N,N′‐bis‐2‐cyanoethyl‐
o
‐phenylenediamine

product: N,N′‐bis‐2‐cyanoethyl‐
p
‐phenylenediamine

product: N‐2‐Cyanoethylaniline
Cyclodecanone
Authors: Cope Arthur C. , Barthel John W. , Smith Ronald Dean
Published: November 2003

Cyclodecanone

product: cyclodecane, cyclodecanone

product: cyclodecane
Diazomethane
Authors: de Boer J. , Backer H. J.
Published: November 2003

Diazomethane

solvent: 35 ml. of Carbitol

product: diazomethane
β‐Ethyl‐β‐methylglutaric acid
Authors: Farmer H. H. , Rabjohn Norman
Published: November 2003

β‐Ethyl‐β‐Methylglutaric acid

intermediate: 280 g. (1.36 moles) of α,α′‐dicyano‐β‐ethyl‐β‐methylglutarimide

product: β‐ethyl‐β‐methylglutaric acid
Ferrocene
Authors: Wilkinson G.
Published: November 2003

Ferrocene

reactant: 42 ml. (0.5 mole) of cyclopentadiene

product: ferrocene

solvent: petroleum ether

reactant: dicyclopentadienylnickel
2‐Furoic Acid
Authors: Harrisson R. J. , Moyle M.
Published: November 2003

2‐Furoic acid

product: 2‐furoic acid
n‐Hexyl Fluoride
Authors: Vogel Arthur I. , Leicester James , Macey William A. T.
Published: November 2003

n‐Hexyl fluoride

solvent: 200 g. of dry ethylene glycol

reactant: 165 g. (1.0 mole) ofn‐hexyl bromide

product:n‐hexyl fluoride
6‐Hydroxynicotinic Acid
Authors: Boyer J. H. , Schoen W.
Published: November 2003

6‐Hydroxynicotinic acid

intermediate: methyl coumalate

product: 6‐hydroxynicotinic acid
3‐Methyl‐4‐nitropyridine‐1‐oxide
Authors: Taylor E. C. , Crovetti Aldo J.
Published: November 2003

3‐Methyl‐4‐nitropyridine‐1‐oxide

reactant: One hundred and eighty grams (1.65 moles) of liquefied 3‐methylpyridine‐1‐oxide

reactant: 200 g. (2.15 moles) of freshly distilled 3‐methylpyridine

product: 3‐Methyl‐4‐nitropyridine‐1‐oxide
o
‐ and
p
‐Nitrobenzaldiacetate
Authors: Nishimura Tamio
Published: November 2003

o
‐ and
p
‐Nitrobenzaldiacetate

product:
p
‐
nitrobenzaldiacetate
.

reactant: 50 g. (0.36 mole) of
p
‐nitrotoluene

byproduct:
p
‐nitrobenzoic acid

product:
p
‐nitrobenzaldehyde

product:
o
‐nitrobenzaldiacetate
N‐Phenylbenzamidine
Authors: Cooper F. C. , Partridge M. W.
Published: November 2003

N‐phenylbenzamidine

product: N‐phenylbenzamidine
Sebacoin
Authors: Allinger Norman L.
Published: November 2003

Sebacoin

solvent: 900 ml. of xylene

reactant: 115 g. (0.50 mole) of dimethyl sebacate

product: Sebacoin
α‐Sulfopalmitic Acid
Authors: Weil J. K. , Bistline R. G. , Stirton A. J.
Published: November 2003

α‐Sulfopalmitic acid

reactant: Palmitic acid (200 g., 0.78 mole)

reactant: sulfur trioxide, 53 ml. (100 g., 1.25 moles)

product: α‐Sulfolauric acid

product: α‐Sulfomyristic acid

product: α‐Sulfopalmitic acid

product: α‐Sulfostearic acid

product: α‐Sulfobehenic acid
Benzofurazan Oxide
Authors: Mallory F. B. , Smith P. A. S. , Boyer J. H.
Published: November 2003

Benzofurazan oxide

reactant:
o
‐Nitroaniline (40 g., 0.29 mole)

product: benzofurazan oxide

intermediate:
o
‐nitrophenylazide
Benzoylacetanilide
Authors: Allen C. F. H. , Humphlett W. J.
Published: November 2003

Benzoylacetanilide

solvent: 100 ml. of petroleum ether

product: Benzoylacetanilide
2‐Chloronicotinonitrile
Authors: Taylor E. C. , Crovetti Aldo J.
Published: November 2003

2‐Chloronicotinonitrile

product: 2‐chloronicotinonitrile
trans‐2‐Dodecenoic Acid
Authors: Allen C. Freeman , Kalm Max J.
Published: November 2003

trans‐2‐Dodecenoic acid

reactant: 30.0 g. (0.15 mole) of dodecanoic acid

product: 2‐dodecenoic acid
Ethyl
tert
‐Butyl Malonate
Authors: Strube R. E.
Published: November 2003

Ethyl
tert
‐butyl malonate

intermediate: 80 g. (0.470 mole) of potassium ethyl malonate

intermediate: monoethyl malonate

product: Ethyl
tert
‐butyl malonate
4‐Ethyl‐2‐methyl‐2‐octenoic acid
Authors: Rinehart Kenneth L. , Perkins Edward G.
Published: November 2003

4‐Ethyl‐2‐methyl‐2‐octenoic acid

reactant: 64.1 g. (0.50 mole) of 2‐ethylhexanal

byproduct: 4‐ethyl‐4‐hydroxy‐2‐methyloctanoic acid, γ‐lactone

product: 4‐ethyl‐2‐methyl‐2‐octenoic acid

intermediate: ethyl 4‐ethyl‐2‐methyl‐3‐hydroxyoctanoate

intermediate: ethyl 4‐ethyl‐2‐methyl‐2‐octenoate

intermediate: ethyl 4‐ethyl‐2‐methyl‐3‐octenoate
Ethyl α‐Nitrobutyrate
Authors: Kornblum Nathan , Blackwood Robert K.
Published: November 2003

Ethyl α‐nitrobutyrate

reactant: Ethyl α‐bromobutyrate (58.5 g., 0.30 mole)

product: ethyl α‐nitrobutyrate

product: Ethyl α‐nitropropionate

product: Ethyl α‐nitrocaproate

product: Ethyl α‐nitroisobutyrate

product: Ethyl α‐nitroisovalerate

product: Ethyl α‐phenyl‐α‐nitroacetate
4‐Hydroxy‐1‐Butanesulfonic Acid Sultone
Authors: Snoddy A. O.
Published: November 2003

4‐Hydroxy‐1‐butanesulfonic acid sultone

product: 4‐Hydroxy‐1‐butanesulfonic acid sultone
Isophorone Oxide
Authors: Wasson Richard L. , House Herbert O.
Published: November 2003

Isophorone oxide

reactant: 55.2 g. (0.4 mole) of isophorone

product: isophorone oxide
3‐Methyloxindole
Authors: Endler Abraham S. , Becker Ernest I.
Published: November 2003

3‐Methyloxindole

intermediate:
β‐Propionylphenylhydrazine

product:
3‐Methyloxindole
.
3‐(
o
‐Chloroanilino)Propionitrile
Authors: Heininger S. A.
Published: November 2003

3‐(
o
‐Chloroanilino)propionitrile

reactant: 255 g. (2.0 moles) of
o
‐chloroaniline

product: 3‐(
o
‐chloroanilino) propionitrile
N‐Ethyl‐
p
‐Chloroaniline
Authors: Roberts Royston M. , Vogt Paul J.
Published: November 2003

N‐ethyl‐
p
‐chloroaniline

intermediate:
N‐Ethyl‐p‐chloroformanilide.

product: N‐ethyl‐
p
‐chloroaniline

byproduct: ethyl N‐
p
‐chlorophenylformimidate

: N‐Methylaniline

: N‐Ethylaniline

: N‐Isoamylaniline

: N‐Methyl‐
m
‐toluidine

: N‐Ethyl‐
m
‐toluidine

: N‐Methyl‐
p
‐chloroaniline
Hendecanedioic Acid
Authors: Durham Lois J. , McLeod Donald J. , Cason James
Published: November 2003

Hendecanedioic acid

product: hendecanedioic acid
β‐Methylglutaric Anhydride
Authors: Cason James
Published: November 2003

β‐Methylglutaric anhydride

reactant: 115 g. (0.72 mole) of diethyl malonate

reactant: 60 g. (0.60 mole) of methyl crotonate

product: β‐Methylglutaric anhydride

product: methyl hydrogen β‐methylglutarate
Methyl Hydrogen Hendecanedioate
Authors: Durham Lois J. , McLeod Donald J. , Cason James
Published: November 2003

Methyl hydrogen hendecanedioate

intermediate: Dimethyl hendecanedioate

product: Methyl hydrogen hendecanedioate
p
‐Dithiane
Authors: Gillis Richard G. , Lacey A. B.
Published: November 2003

p
‐Dithiane

product:
p
‐dithiane
Ethyl (1‐Phenylethylidene)Cyanoacetate
Authors: McElvain S. M. , Clemens David H.
Published: November 2003

Ethyl (1‐phenylethylidene)cyanoacetate

product: Ethyl (1‐phenylethylidene)cyanoacetate
9‐Methylfluorene
Authors: Schoen Kurt L. , Becker E. I.
Published: November 2003

9‐Methylfluorene

reactant: 113 g. (0.68 mole) of fluorene

product: 9‐methylfluorene

product: 9‐Ethylfluorene

product: 9‐
n
‐Propylfluorene

product: 9‐
n
‐Butylfluorene

product: 9‐
n
‐Pentylfluorene

product: 9‐
n
‐Hexylfluorene

product: 9‐
n
‐Heptylfluorene

product: 9‐
n
‐Octadecylfluorene
Phenylpropargylaldehyde Diethyl Acetal
Authors: Howk B. W. , Sauer J. C.
Published: November 2003

Phenylpropargylaldehyde diethyl acetal

product: phenylpropargylaldehyde diethyl acetal

product: cyclohexylmethylpropiolaldehyde diethyl acetal

product: phenylethynyl
n
‐butyl dimethyl ketal

product: phenylethynyl methyl diethyl ketal

product:
n
‐Butylpropiolaldehyde diethyl acetal
Tetraacetylethane
Authors: Charles Robert G.
Published: November 2003

Tetraacetylethane

intermediate: Sodium acetylacetonate is ground to a fine powder in a mortar, and 24.4 g. (0.2 mole) of the anhydrous material or 28.9 g. of the hydrate

product: Tetraacetylethane
Tetracyanoethylene
Authors: Carboni R. A.
Published: November 2003

Tetracyanoethylene

intermediate: Dibromomalononitrile‐potassium bromide complex.

product:
Tetracyanoethylene

reactant: malononitrile was obtained from the Winthrop‐Stearns Corp., New York, N. Y.
α,α,β‐Triphenylpropionitrile
Authors: Hauser C. R. , Dunnavant W. R.
Published: November 2003

α,α,β‐Triphenylpropionitrile

reactant: 30.5 g. (0.24 mole) of benzyl chloride

product: α,α,β‐triphenylpropionitrile
Trithiocarbodiglycolic Acid
Authors: Strube R. E.
Published: November 2003

Trithiocarbodiglycolic acid

reactant: 189 g. (2.0 moles) of chloroacetic acid

product: Trithiocarbodiglycolic acid
3‐Acetyloxindole
Authors: Bunnett J. F. , Hrutfiord B. F. , Williamson S. M.
Published: November 2003

3‐Acetyloxindole

reactant: 105.8 g. (0.5 mole) of
o
‐acetoacetochloroanilide

product: 3‐acetyloxindole

: 2‐phenylbenzothiazole

: 2‐phenylbenzoxazole

: 1‐cyanobenzocyclobutene

: 1‐methyl‐2,1‐benzisothiazoline 2,2‐dioxide
2‐Aminofluorene
Authors: Bavin P. M. G.
Published: November 2003

2‐Aminofluorene

reactant: 30 g. of pure 2‐nitrofluorene

product: 2‐aminofluorene

product: hydrazobenzene
3‐Chloro‐2,2,3‐trifluoropropionic Acid
Authors: England D. C. , Melby L. R.
Published: November 2003

3‐Chloro‐2,2,3‐trifluoropropionic acid

product: 3‐chloro‐2,2,3‐trifluoropropionic acid

byproduct: 3‐chloro‐2,2,3‐trifluoropropionamide
2‐Cyclohexenone
Authors: Gannon Walter F. , House Herbert O.
Published: November 2003

2‐Cyclohexenone

product: 2‐cyclohexenone
4,4′‐Diaminoazobenzene
Authors: Santurri Pasco , Robbins Frederick , Stubbings Robert
Published: November 2003

4,4′‐Diaminoazobenzene

reactant: 29.0 g. (0.19 mole) of
p
‐aminoacetanilide

intermediate: 4,4′‐bis(acetamido)azobenzene

product: 4,4′‐diaminoazobenzene
1,4‐Diphenyl‐1,3‐Butadiene
Authors: McDonald Richard N. , Campbell Tod W.
Published: November 2003

1,4‐Diphenyl‐1,3‐Butadiene

intermediate: 60.0 g. (0.145 mole) of triphenylcinnamylphosphonium chloride

product: 1‐(
p
‐tolyl)‐4‐phenylbutadiene

product: 1‐(4‐methoxyphenyl)‐4‐phenylbutadiene

product: 1‐(4‐acetamidophenyl)‐4‐phenylbutadiene

product: 1,4‐Diphenylbutadiene
3‐Ethoxy‐2‐Cyclohexenone
Authors: Gannon Walter F. , House Herbert O.
Published: November 2003

3‐Ethoxy‐2‐cyclohexenone

product: 3‐ethoxy‐2‐cyclohexenone
Ethyl 6,7‐Dimethoxy‐3‐Methylindene‐2‐Carboxylate
Authors: Koo John
Published: November 2003

Ethyl 6,7‐dimethoxy‐3‐methylindene‐2‐carboxylate

product: ethyl 6,7‐dimethoxy‐3‐methylindene‐2‐carboxylate
3‐(2‐Furyl)acrylonitrile
Authors: Patterson John M.
Published: November 2003

3‐(2‐Furyl)acrylonitrile

product: 3‐(2‐Furyl)acrylonitrile
Hydroxymethylferrocene
Authors: Lednicer Daniel , Mashburn T. Arthur , Hauser Charles R.
Published: November 2003

Hydroxymethylferrocene

product: hydroxymethylferrocene
3‐Hydroxyquinoline
Authors: Cragoe Edward J. , Robb Charles M.
Published: November 2003

3‐Hydroxyquinoline

reactant: 249 g. (2.83 moles) of pyruvic acid

intermediate: chloropyruvic acid

intermediate: 3‐Hydroxycinchoninic acid (part B) (94.6 g., 0.5 mole)

product: 3‐hydroxyquinoline

reactant: monohydrate
N‐Phthalyl‐
L
‐β‐phenylalanine
Authors: Bose Ajay K.
Published: November 2003

N‐phthalyl‐
L
‐β‐phenylalanine

product: N‐phthalyl‐
L
‐β‐phenylalanine

reactant: 16.5 g. (0.1 mole) of
L
‐phenylalanine

product:
N
‐phthalyl‐β‐alanine

product: N‐phthalyl‐
L
‐alanine

product: ethyl ester of N‐phthalylglycine
p
‐Quinquephenyl
Authors: Campbell Tod W. , McDonald Richard N.
Published: November 2003

p
‐Quinquephenyl

intermediate: 70 g. (0.10 mole) of
p
‐xylylene‐bis(triphenylphosphonium chloride)

intermediate: 3.34 g. (0.010 mole) of 1,4‐bis‐(4‐phenylbutadienyl)benzene

reactant: 1,4‐bis‐[4‐(
p
‐tolyl)butadienyl]benzene

reactant: 1,4‐bis‐[4‐(3‐nitrophenyl)butadienyl]‐benzene

reactant: 1,4‐bis‐(3‐methyl‐4‐phenylbutadienyl)benzene

product:
p
‐Quinquephenyl
p
‐Toluenesulfonylhydrazide
Authors: Friedman Lester , Litle Robert L. , Reichle Walter R.
Published: November 2003

p
‐Toluenesulfonylhydrazide

product:
p
‐Toluenesulfonylhydrazide
Triphenylene
Authors: Heaney H. , Millar I. T.
Published: November 2003

Triphenylene

intermediate:
o
‐bromoiodobenzene

product: triphenylene
2,7‐Dimethyl‐2,7‐Dinitroöctane
Authors: Sharkey W. H. , Langkammerer C. M.
Published: November 2003

2,7‐Dimethyl‐2,7‐dinitroöctane

reactant: 4‐methyl‐4‐nitrovaleric acid

product: 2,7‐dimethyl‐2,7‐dinitroöctane
Dimethyl Octadecanedioate
Authors: Swann Sherlock , Garrison W. E.
Published: November 2003

Dimethyl octadecanedioate

product: dimethyl octadecanedioate
1,6‐Dioxo‐8a‐Methyl‐1,2,3,4,6,7,8,8a‐Octahydronaphthalene
Authors: Ramachandran S. , Newman Melvin S.
Published: November 2003

1,6‐Dioxo‐8a‐methyl‐1,2,3,4,6,7,8,8a‐octahydronaphthalene

product: 1,6‐dioxo‐8a‐methyl‐1,2,3,4,6,7,8,8a‐octahydronaphthalene

intermediate: 2‐methyl‐2‐(3′‐oxobutyl)‐1,3‐cyclohexanedione

solvent: hexane
Diphenaldehyde
Authors: Bailey Philip S. , Erickson Ronald E.
Published: November 2003

Diphenaldehyde

reactant: 10.0 g. (0.056 mole) of phenanthrene

product: diphenaldehyde
1‐Morpholino‐1‐Cyclohexene
Authors: Hünig S. , Lücke E. , Brenninger W.
Published: November 2003

1‐Morpholino‐1‐cyclohexene

product: 1‐Morpholino‐1‐cyclohexene
2‐Nitroethanol
Authors: Noland Wayland E.
Published: November 2003

2‐Nitroethanol

reactant: nitromethane (2.5 l., 46.6 moles)

unknown: diphenyl ether

product: 2‐nitroethanol

solvent: petroleum ether
2‐Oxa‐7,7‐dichloronorcarane
Authors: Parham William E. , Schweizer Edward E. , Mierzwa Sigmund A.
Published: November 2003

2‐Oxa‐7,7‐dichloronorcarane

solvent: 100‐ml. portions of petroleum ether

product: 2‐oxa‐7,7‐dichloronorcarane
1,1,1‐Trifluoroheptane
Authors: Hasek W. R.
Published: November 2003

1,1,1‐Trifluoroheptane

product: 1,1,1‐Trifluoroheptane

product: 1,1,1‐Trifluorododecane

product: 1,1,1‐Trifluorohexadecane

product: 1,1,1‐Trifluoro‐3,5,5‐trimethylhexane

product: (4,4,4‐Trifluorobutyl)cyclohexane

product: 1,1,1,10,10,10‐Hexafluorodecane

product: 1,1,1,6,6,6‐Hexafluoro‐3‐hexene

product:
p
‐Bis(trifluoromethyl)benzene

product: 2,4‐Bis(trifluoromethyl)chlorobenzene

product:
p
‐Trifluoromethylnitrobenzene
Acetone Dibutyl Acetal
Authors: Lorette N. B. , Howard W. L.
Published: November 2003

Acetone dibutyl acetal

product: acetone dibutyl acetal
1‐Benzylpiperazine
Authors: Craig J. Cymerman , Young R. J.
Published: November 2003

1‐Benzylpiperazine

intermediate: piperazine dihydrochloride monohydrate

intermediate: 1‐benzylpiperazine dihydrochloride

product: 1‐benzylpiperazine

byproduct: 1‐benzyl‐4‐piperazinium chloride

byproduct: 1‐benzoyl‐4‐benzylpiperazine hydrochloride
3‐Bromophthalide
Authors: Koten I. A. , Sauer Robert J.
Published: November 2003

3‐Bromophthalide

product: 3‐bromophthalide

product: phthalaldehydic acid
t
‐Butyl acetoacetate
Authors: Lawesson Sven‐Olov , Gronwall Susanne , Sandberg Rune
Published: November 2003

t
‐Butyl acetoacetate

product:
t
‐Butyl acetoacetate
2,2‐Difluorosuccinic Acid
Authors: Raasch M. S. , Castle J. E.
Published: November 2003

2,2‐Difluorosuccinic acid

intermediate: 1,1,2‐trichloro‐2,3,3‐trifluorocyclobutane

intermediate: 1‐chloro‐2,3,3‐trifluorocyclobutene

product: 2,2‐difluorosuccinic acid
1,2‐Dimercaptobenzene
Authors: Ferretti Aldo
Published: November 2003

1,2‐Dimercaptobenzene

product: 1,2‐dimercaptobenzene
N‐Iodosuccinimide
Authors: Benson W. R. , McBee E. T. , Rand L.
Published: November 2003

N‐iodosuccinimide

reactant: Eighteen grams (0.087 mole) of thoroughly dried N‐silver succinimide

product: N‐Iodosuccinimide
Monoperphthalic Acid
Authors: Payne George B.
Published: November 2003

Monoperphthalic acid

product: monoperphthalic acid
2,3,4,5‐Tetramethylpyrrole
Authors: Johnson A. W. , Price R.
Published: November 2003

2,3,4,5‐Tetramethylpyrrole

product: 2,3,4,5‐Tetramethylpyrrole
Thiobenzoylthioglycolic Acid
Authors: Kurzer Frederick , Lawson Alexander
Published: November 2003

Thiobenzoylthioglycolic Acid

product: Thiobenzoylthioglycolic acid
α‐Benzylidene‐γ‐Phenyl‐Δ
β,γ
‐Butenolide
Authors: Filler Robert , Piasek Edmund J. , Leipold Hans A.
Published: November 2003

α‐Benzylidene‐γ‐phenyl‐Δ
β,γ
‐butenolide

product: α‐benzylidene‐γ‐phenyl‐Δ
β,γ
‐butenolide
2‐Bromoallylamine
Authors: Bottini Albert T. , Dev Vasu , Klinck Jane
Published: November 2003

2‐Bromoallylamine

intermediate: 2‐bromoallylhexaminium bromide

product: 2‐bromoallylamine
N‐Ethylpiperidine
Authors: Wollensak J. , Closson R. D.
Published: November 2003

N‐Ethylpiperidine

reactant: 340 g. (4.00 moles) of piperidine

product: N‐ethylpiperidine
p
‐Hydroxyphenylpyruvic Acid
Authors: Billek Gerhard
Published: November 2003

p
‐Hydroxyphenylpyruvic acid

reactant: 6.11 g. (0.050 mole) of
p
‐hydroxybenzaldehyde

intermediate: 5‐(
p
‐hydroxybenzal)hydantoin

product:
p
‐hydroxyphenylpyruvic acid
Iodosobenzene
Authors: Saltzman H. , Sharefkin J. G.
Published: November 2003

Iodosobenzene

product: iodosobenzene
Iodoxybenzene
Authors: Sharefkin J. G. , Saltzman H.
Published: November 2003

Iodoxybenzene

product: iodoxybenzene
1,2,3,4,5‐Pentachloro‐5‐ethylcyclopentadiene
Authors: Mark V. , Wann R. E. , Godt H. C.
Published: November 2003

1,2,3,4,5‐Pentachloro‐5‐ethylcyclopentadiene

reactant: 183 g. (1.10 moles) of triethyl phosphite

solvent: 200 ml. of petroleum ether

product: 1,2,3,4,5‐pentachloro‐5‐ethylcyclopentadiene

reactant: diethyl hydrogen phosphite

reactant: triethyl phosphate

byproduct: diethyl phosphorochloridate [chlorodiethoxyphosphorus (V) oxide]
7‐
t
‐Butoxynorbornadiene
Authors: Story Paul R. , Fahrenholtz Susan R.
Published: November 2003

7‐
t
‐Butoxynorbornadiene

solvent: 500 ml. of benzene

product: 7‐t‐butyoxynorbornadiene

product: 7‐benzoxynorbornadiene
t
‐Butyl azidoformate
Authors: Carpino Louis A. , Carpino Barbara A. , Crowley Paul J. , Giza Chester A. , Terry Paul H.
Published: November 2003

t
‐Butyl azidoformate

product:
t
‐Butyl azidoformate
t
‐Butyl azodiformate
Authors: Carpino Louis A. , Crowley Paul J.
Published: November 2003

t
‐Butyl azodiformate

solvent: 60 ml. of pyridine

intermediate: 23.2 g. (0.1 mole) of crude
t
‐butyl hydrazodiformate

solvent: 35–40 ml. of petroleum ether

solvent: ligroin

product:
t
‐Butyl azodiformate
Cyclopropylbenzene
Authors: Corbin Thomas F. , Hahn Roger C. , Shechter Harold
Published: November 2003

Cyclopropylbenzene

intermediate: 1,3‐dibromo‐1‐phenylpropane

product: cyclopropylbenzene
Ethyl β‐Hydroxy‐β,β‐Diphenylpropionate
Authors: Dunnavant W. R. , Hauser Charles R.
Published: November 2003

Ethyl β‐hydroxy‐β,β‐diphenylpropionate

product: ethyl β‐hydroxy‐β,β‐diphenylpropionate

reactant: benzophenone

product: Isopropyl and
t
‐butyl β‐hydroxy‐β,β‐diphenylpropionate
Indole‐3‐acetic Acid
Authors: Johnson Herbert E. , Crosby Donald G.
Published: November 2003

Indole‐3‐acetic acid

product: indole‐3‐acetic acid
Peroxybenzoic Acid
Authors: Silbert Leonard S. , Siegel Elaine , Swern Daniel
Published: November 2003

Peroxybenzoic acid

product: peroxybenzoic acid
2
a
‐Thiohomophthalimide
Authors: Smith P. A. S. , Kan R. O.
Published: November 2003

2
a
‐Thiohomophthalimide

intermediate:
Phenylacetyl isothiocyanate

product:
2a‐Thiohomophthalimide

reactant: Lead thiocyanate

product: 6‐methyl‐1
a
‐thiophthalimide

product: 4,6‐dimethyl‐1
a
‐thiophthalimide

product: 5‐methyl‐2
a
‐thiohomophthalimide

product: 4‐methyl‐2
a
‐thiohomophthalimide

product: 5‐methoxy‐2
a
‐thiohomophthalimide

product: 4‐chloro‐2‐thiohomophthalimide

product: 1
a
‐phenyl‐2
a
‐thiohomophthalimide

product: 1
a
‐thio‐1,2‐naphthalimide

product: 2
a
‐thio‐1‐homo‐1,2‐naphthalimide

product: thiophene‐2
a
‐thio‐2,3‐dicarboximide
Phenylsulfur Trifluoride
Authors: Sheppard William A.
Published: November 2003

Phenylsulfur trifluoride

solvent: 500 ml. of 1,1,2‐trichloro‐1,2,2‐trifluoroethane

product: phenylsulfur trifluoride
Benzoyl Fluoride
Authors: Olah George A. , Kuhn Stephen J.
Published: November 2003

Benzoyl fluoride

product: benzoyl fluoride

product: Propionyl fluoride

product:n‐Butyryl fluoride

product: Isobutyryl fluoride

product: Valeryl fluoride

product: Isovaleryl fluoride

product: Caproyl fluoride

product: Heptanoyl fluoride

product: Octanoyl fluoride

product: Pelargonyl fluoride

product: Decanoyl fluoride

product: Fluoroacetyl fluoride

product: Chloroacetyl fluoride

product: Dichloroacetyl fluoride

product: Trichloroacetyl fluoride

product: Bromoacetyl fluoride

product: Phthaloyl fluoride

product: Phenylacetyl fluoride
2‐Benzylcyclopentanone
Authors: Elsinger Fritz
Published: November 2003

2‐Benzylcyclopentanone

intermediate: 2‐benzyl‐2‐carbomethoxycyclopentanone

product: 2‐benzylcyclopentanone

solvent: 2,6‐lutidine
D
,
L
‐10‐Camphorsulfonyl Chloride
Authors: Bartlett Paul D. , Knox L. H.
Published: November 2003

D
,
L
‐10‐Camphorsulfonyl chloride

product: 10‐Camphorsulfonyl chloride
γ‐Crotonolactone
Authors: Price Charles C. , Judge Joseph M.
Published: November 2003

γ‐crotonolactone

intermediate:α‐Bromo‐γ‐butyrolactone.

product: Δα,β‐Butenolide.

byproduct: β‐hydroxy‐γ‐butyrolactone
1,4‐Cyclohexanedione
Authors: Nielsen Arnold T. , Carpenter Wayne R.
Published: November 2003

1,4‐Cyclohexanedione

intermediate: 2,5‐dicarbethoxy‐1,4‐cyclohexanedione

product: 1,4‐cyclohexanedione
Diphenyldiacetylene
Authors: Campbell I. D. , Eglinton G.
Published: November 2003

Diphenyldiacetylene

solvent: 50 ml. of petroleum ether

product: diphenyldiacetylene
Ethyl Cyclohexylideneacetate
Authors: Wadsworth W. S. , Emmons William D.
Published: November 2003

Ethyl cyclohexylideneacetate

reactant: 74.7 g. (0.33 mole) of triethyl phosphonoacetate

product: Ethyl cyclohexylideneacetate
Ketene
Authors: Andreades S. , Carlson H. D.
Published: November 2003

Ketene

product: ketene

reactant: diketene

byproduct: dehydroacetic acid
18,20‐Lactone of 3β‐Acetoxy‐20β‐Hydroxy‐5‐Pregnene‐18‐Oic Acid
Authors: Heusler K. , Wieland P. , Meystre Ch.
Published: November 2003

18,20‐Lactone of 3β‐acetoxy‐20β‐hydroxy‐5‐pregnene‐18‐oic acid

intermediate:
3β‐Acetoxy‐20β‐hydroxy‐5‐pregnene

reactant: 71.7 g. (0.2 mole) of pregnenolone acetate

intermediate:
3β‐Acetoxy‐18‐iodo‐ and 18‐hydroxy‐18,20β‐oxido‐5‐pregnene

product: 18,20‐lactone of 3β‐acetoxy‐20β‐hydroxy‐5‐pregnene‐18‐oic acid
Nortricyclanone
Authors: Meinwald J. , Crandall J. , Hymans W. E.
Published: November 2003

Nortricyclanone

product: nortricyclanone
Triphenylaluminum
Authors: Neely T. A. , Schwarz William W. , Vaughan Herbert W.
Published: November 2003

Triphenylaluminum

intermediate: triphenylaluminum etherate

product: triphenylaluminum

byproduct: mercury
Chloromethylphosphonothioic Dichloride
Authors: Schmutzler R.
Published: November 2003

Chloromethylphosphonothioic dichloride

product: Chloromethylphosphonothioic dichloride
Coumarone
Authors: Burgstahler Albert W. , Worden Leonard R.
Published: November 2003

Coumarone

intermediate:
o‐Formylphenoxyacetic acid
.

product: benzofuran

byproduct: coumarilic acid
Formamidine Acetate
Authors: Taylor Edward C. , Ehrhart Wendell A. , Kawanisi M.
Published: November 2003

Formamidine acetate

reactant: 90.0 g. of triethyl orthoformate

product: Formamidine acetate
β‐Isovalerolactam‐N‐Sulfonyl Chloride and β‐Isovalerolactam
Authors: Graf Roderich
Published: November 2003

β‐Isovalerolactam‐N‐sulfonyl chloride and β‐isovalerolactam

product: β‐isovalerolactam‐N‐sulfonyl chloride

product: β‐
Isovalerolactam
Methyl Isocyanide
Authors: Schuster R. E. , Scott James E. , Casanova Joseph
Published: November 2003

Methyl isocyanide

product: Methyl isocyanide

reactant: Quinoline, practical grade

product: methyl (50%), ethyl (45%), s‐butyl (35%) and cyclobutyl (24%) isocyanides
Methyl Phenyl Sulfoxide
Authors: Johnson Carl R. , Keiser Jeffrey E.
Published: November 2003

Methyl phenyl sulfoxide

reactant: methyl phenyl sulfoxide

product: Methyl 4‐ketopentyl sulfoxide

product: Thian 1‐oxide

product: 1,4‐Oxathian 1‐oxide

product: Bis(2‐diethylaminoethyl)sulfoxide

product: Acetoxymethyl methyl sulfoxide

product: 1‐Benzylsulfinyl‐2‐propanone

product: Phenylsulfinylacetic acid

product: Benzyl sulfoxide

product: Ethyl sulfoxide

product: Ethyl phenyl sulfoxide
2‐Nitrocarbazole
Authors: Mendenhall G. David , Smith Peter A. S.
Published: November 2003

2‐Nitrocarbazole

intermediate:
o
‐aminobiphenyl

intermediate:
o‐Amino‐p′‐nitrobiphenyl

intermediate:
o‐Azido‐p′‐nitrobiphenyl

product: 2‐Nitrocarbazole
Palladium Catalyst for Partial Reduction of Acetylenes
Authors: Lindlar H. , Dubuis R.
Published: November 2003

Palladium catalyst for partial reduction of acetylenes

product: 0.10 g. of the palladium

solvent: 15 ml. of olefin‐free petroleum ether
α‐Pyrone
Authors: Zimmerman Howard E. , Grunewald Gary L. , Paufler Robert M.
Published: November 2003

α‐Pyrone

reactant: 37.5‐g. (0.266‐mole) sample of coumalic acid

product: α‐pyrone
Triethyloxonium Fluoborate
Authors: Meerwein H.
Published: November 2003

Triethyloxonium fluoborate

product: triethyloxonium fluoborate
Trimethyloxonium 2,4,6‐Trinitrobenzenesulfonate
Authors: Helmkamp G. K. , Pettitt D. J.
Published: November 2003

Trimethyloxonium 2,4,6‐trinitrobenzenesulfonate

reactant: 2,4,6‐Trinitrobenzenesulfonic acid (14.7 g., 0.050 mole)

product: trimethyloxonium 2,4,6‐trinitrobenzenesulfonate

byproduct: methyl 2,4,6‐trinitrobenzenesulfonate