Manufacture of Alkyl Glycolio Acid Derivatives of Paramidophenol Ethers.COLIC ACID PHENETIDIDE FROM CHLORACET- PHENETIDIDE AND ALCOHOLATE OF SODIUM
Year: 1896

page_text: Date of Application, 25th Apr., 1896-Accepted, 6th June, 1896
[Communicated from abrond by BASLE CHEMICAL WORKS BINDSCHEDLER, of
Basle, Switzerland, Manufacturers.]
Manufacture of Alkyl Glycolio Acid Derivatives of Paramidophenol
Ethers.
1, HAROLD IMRAY, of No. 28 Southampton Buildings, Chancery Lano, in the
County of London. Chartered Patent Agent, do hereby declare the nature of this
invention and in what manner the same is to be performed to be particularly
described and arcertained in and by the following statement:-
My foreign correspondents have found that the mono halogen acetic acid
derivatives of p. amidophenol ethers, as for instance the obloracetphenetitide
derived from chloride of chloracetic acid and p. phenetidine, on being heated with
alcoholates of sodium, are smoothly transformed, into alkyl glycolic acid derivatives
of p. amidophenol ethers, which have valuable antipyretic and anti neuralgic
properties and are therefore suitable for use in medicine and pharmacy.
In this manner are obtained, for instance, from chloracetphenetidide and methyl
alcoholate of sodium the methyl glycolic acid derivative of phenetidine or methyl
glycolic acid phenetidide, according to the following equation :
paraminophenolether.
Thus, for instance, is formed the ethyl glycolic acid paraphenetidido from alkyl
glycolic acid and p-phenetidine as shewn by the following equation:
C,H,OCH,COOH + H,NC,H,OC,H, = C,H,OCH,CONHC,H,OC,H, + H₂O
PRODUCTION OF METHYL GLYCOLIC ACID PHENETIDIDE FROM CHLORACET-
PHENETIDIDE AND ALCOHOLATE OF SODIUM.
5-65 kilos, of chloride of chloracetic acid dissolved in 5 litres of dry ether are
mixed slowly by shaking and refrigerating with a solution of 13-7 kilos. phonetidine
in 50 litres dry ether.
A white pulverised product is separated, consisting of phenetidine hydrochloride
and chloracet-phenetidide, which is filtered and which, to remove the phenetidine
bydrochlorate, is washed with warm water.
water. The chloracet-phenetidide not
dissolved is recrystallised with alcohol and white needles are produced having a
melting point of 145° to 146° C.
To a solution of 10. kilos. of the monochloracetphenetidide so produced in
120 kilos. of methyl alcohol, is added a solution of 1077 grammes of sodium in
15 kilos. of methylalcohol and this mixture is heated to the boiling point. From
this results a quick separation of sodium chloride after a few hours boiling the

page_text: quantity of sodium chloride increases no farther and then the methylalcohol is
distilled off and the sediment, by treatment with water, is freed from sodium
chloride. The solid. product of reaction is recrystallised with hot water.
The methyl glycolic acid phenetidide forms white silky needles, which melt
at 101 to 102° C.
EXAMPLE II.
PRODUCTION OF METHYL GLYCOLIC ACID PHENETI DIDE FROM ALKYL
GLYCOLIC ACID AND P-PHENETIDINE.
100 kilos. of p-phenctidine are heated with 70 kilos. of methyl glycolic acid
during several hours to 1300-140° C.
The product of the reaction is washed in cold water and recrystallised from hot
water. If necessary, the solution is purified with animal charcoal. The product
crystallises in form of white needles having a melting point of 101°-102° C.
Having now particularly described and ascertained the nature of this invention
and in what manner the saine is to be performed, I declare that what i
claim is :-
1. The herein described manufacture of alkyl glycolic acid derivatives of
paramidophenol ethers, by the reaction:
a) of the mono halogen acetic acid derivatives of p-amidophenol ethers with
alcoholates of sodium, and
b) of the alkyl glycolic acids with paramidophenolethers.
2. The alkyl glycolic acid derivatives of paramido phenol ethers, manufactured
as above set forth.
Dated this 25th day of April 1896.
ABEL & IMRAY,
Agents for the Applicant.