Manufacture of Basic Phenol Ethers.
Year: 1898

page_text: Date of Application, 7th Nov., 1898
Complete Specification Left, 7th July, 1899-Accepted, 12th Aug., 1899
PROVISIONAL SPECIFICATION,
Manufacture of Basic Phenol Ethers.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, Chancery
Lane, in the County of London, Chartered Patent Agent, do hereby declare the
nature of this invention (as communicated to me from abroad by The Farbwerke
vormals Meister Lucius and Britning of Hoechst a/Main, in the Empire of Germany,'
Chemical Manufacturers,) to be as follows:-
If halogenacidyl phenols, produced by the reaction between phenols and halogen
substituted acid halides, be combined with secondary amines, a series of new phenol
derivatives may be obtained, which by the amine residue entering the molecule are
basic compounds and as such are capable of forming salts soluble in water. These
derivatives are inodorous, not poisonous, and of strong antiseptic power; they may be
called glycocollphenol ethers.
The following example illustrates the manufacture of such glycocollphenol
ethers :-
To a solution of 50 parts by weight of guaiacol and 230 parts by weight of mono-
chloracetic acid in 100 parts by weight of pyridine are added, while the mixture is
cooled 65 parts by weight of POC!, and the liquid is heated for about 2 hours on
the waterbath.
When cold, the product of reaction is poured into water. The resulting chloracetyl-
guaiacol soon separates, partly as a solid white mass and partly as an oil which
soon solidifies. The compound crystallises from absolute alcohol in long white
needles having a melting point of 58°-60° C.
To 43 parts by weight of chloracetylguaiacol are added, while stirring, 35 parts by
weight of diethylamine; a lively reaction soon sets in, which is moderated by cooling
with ice.
The chloracetylguaiacol dissolves gradually and after 2 hours the mass, having
become gelatinous, is treated with dilute soda solution and extracted with ether.
This extract, previously shaken with soda lye, in order to remove the regenerated
guaiacol, leaves behind on evaporation the diethylglycocollguaiacol as a thick basic
oil, which is purified by conversion into its hydrobromide; this salt separates from
water in white needles having a melting point of 208° C. and crystallises from an
alcoholic solution on addition of ether.
Dated this 7th day of November 1898.
ABEL & IMRAY,
Agents for the Applicant.
I, OLIVER IMRAY, of Birkbeck Bank Chambers, Southampton Buildings, Chancery
Lane,, in the County of London, Chartered Patent Agent, do hereby declare the
[Price 811

page_text: nature of this invention (as communicated to me from abroad by The Farbwerke
vormals Meister Lucius and Brüning, of Hoechst a/Main, in the Empire of Germany,
Chemical Manufacturers,) and in what manner the same is to be performed to
be particularly described and ascertained in and by the following statement :-
If halogenacidyl phenols, produced by the reaction between phenols and halogen
substituted acid halides, be treated with secondary amines a series of new phenol
derivatives may be obtained, which by the amine residue entering the molecule are
basic compounds and as such are capable of forming salts soluble in water. These
derivatives are inodorous; not poisonous, and of strong antiseptic power; they may be
called glycocollphenol ethers.
The following example illustrates the manufacture of such glycocollphenol
ethers :-
To a solution of 50 parts by weight of guaiacol and 230 parts by weight of monochlor-
acetic acid in 100 parts by weight of pyridine are added, while the mixture is cooled,
65 parts by weight of POCI, and the liquid is heated for about 2 hours on the water-
bath.
When cold, the product of reaction is poured into water. The resulting chloracetyl-
guaiacol soon separates, partly as a solid white mass and partly as an oil which soon
solidifies.
The compound crystallises from absolute alcohol in long white needles having a
melting point of 58°-60° C.
To 43 parts by weight of chloracetylguaiacol are added, while stirring, 35 parts by
weight of diethylamine; a lively reaction soon sets in, which is moderated by cooling
with ice.
The chloracetylguaiacol dissolves gradually and after 2 hours the mass, having
become gelatinous, is treated with dilute soda solution and extracted with ether. This
extract, previously shaken with soda lye in order to remove the generated guaiacol,
leaves behind on evaporation the diethylglycocollguaiacol as a thick basic oil, which
is purified by conversion into its hydrobromide; this salt separates from water in
white needles having a melting point of 208° C. and crystallises from an alcoholic
solution on addition of ether.
In a corresponding manner other glycocollphenolesters may be obtained, for
instance:-
di-isobutylglycocollguaiacol, an oil; its hydriodic salt melts at 145° C.
diethylglycocolicresol, an oil; its chlorhydrate melts at 176°.
diethylglycocoll-phenol, an oil; its chlorhydrate melts at 165°.
diethylglycocoli-o-cresol, an oil; its bromehydrate melts at 164º.
diethylglycocoll-m-cresol, an oil; its chlorhydrate melts at 173°.
diethylglycocoll-p-cresol, an oil; its picrate melts at 129°.
C
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
1. The herein described manufacture of glycocollphenolesters, by treating the
chloro-acetic esters of phenols with secondary amines.
2. Glycocollphenolesters manufactured as above set forth.
Dated this 3rd day of July 1899