GB1140748A — New carboxylic acid derivatives

USPTO Abstract

1,140,748. Carboxylic acid derivatives. IMPERIAL CHEMICAL INDUSTRIES Ltd. 30 May, 1967 [23 June, 1966 (2)], Nos. 28198/66 and 28200/66. Heading C2C. [Also in Division A5] Novel carboxylic acid derivatives of the general formula wherein X is an oxygen or sulphur atom or an imino or sulphonyl radical; Y is a direct linkage or an oxygen or sulphur atom or a sulphonyl or -CR<SP>1</SP>R<SP>2</SP>- radical; R<SP>1</SP> and R<SP>2</SP>, which may be the same or different, are hydrogen atoms or alkyl radicals; and the ring B is optionally substituted by one or more substituents selected from halogen atoms and alkyl radicals; and esters, amides and salts thereof are prepared by reaction of a metal derivative of the formula wherein X<SP>1</SP> is an oxygen or sulphur atom and M is a metal atom, with a carboxylic acid of the formula Z-CR<SP>1</SP>R<SP>2</SP>-COOH, wherein Z is a halogen atom, or an ester, amide or salt thereof, or by reaction of a halogen derivative of the formula with an ester, amide or salt of a carboxylic acid of the formula M-X<SP>2</SP>-CR<SP>1</SP>R<SP>2</SP>-COOH, wherein X<SP>2</SP> is an oxygen or sulphur atom or an imino radical; whereafter, if desired, the product of the first formula above wherein either or both of X and Y are sulphur atoms is oxidized to the corresponding compound wherein either or both of X and Y are sulphonyl radicals; whereafter, if desired, the resulting carboxylic acid or salt thereof is converted to an ester or amide thereof by conventional means, a resulting ester is converted to an amide thereof by conventional means, or a resulting ester or amide is hydrolysed to the corresponding carboxylic acid or salt thereof by conventional means. 4 - (p - Chlorophenyl) - benzyl alcohol is prepared by hydrolysis of 4-(p-chlorophenyl)- benzyl chloride. 4 - (p - Chlorophenoxy). benzyl chloride and 4-(p-chlorophenyl)-benzyl chloride are prepared by treating 4-chlorodiphenyl ether and 4-chlorobiphenyl, respectively, with ethoxymethyl chloride and stannic chloride 4-(p-Tolylthio)-benzyl alcohol is obtained by reacting p-thiocresol with ethyl p-aminobenzoate in the presence of sodium nitrite and hydrochloric acid and reducing the resulting 4 - (p - tolylthio) - benzoic acid with lithium aluminium hydride. 4-(p-Chlorobenzyl)-benzyl alcohol is prepared by treating 4-chloro-4<SP>1</SP>- methylbenzophenone with gaseous chlorine, converting the resulting 4-(p-chlorobenzoyl)- benzyl chloride to 4-(p-chlorobenzoyl)-benzyl acetate with acetic acid and reducing the said acetate.