GB594624A - Process for the preparation of benzyl alcohols substituted by a dialkylaminomethyl group and, if desired, an alkoxy group - Google Patents

Abstract

Amino arylaliphatic alcohols having the general formula: <FORM:0594624/IV/1> (wherein R represents an alkyl group and in which the benzene nucleus may contain alkoxy groups) are obtained by reducing the corresponding dialkyl aminobenzoic acid or its ester or the corresponding aldehyde by known methods. They may also be obtained by condensing a dialkylamine with an alkyl ether of a chloromethylbenzyl alcohol, treating the product with hydrobromic acid to replace the alkloxy group by a bromine atom, replacing the bromine atom by an ester group, and removing the ester group by hydrolysis. In examples: (1) and (2) p-diethylaminomethylbenzyl alcohol is obtained by: (1) reducing the ethyl ester of p-(w-diethylamino)- toluic acid by sodium dissolved in alcohol; (2) heating the methyl ether of 4-chloro-methyl-benzyl alcohol with diethylamine in alcoholic solution to obtain 1 - methoxymethyl - 4 - diethylaminomethyl-benzene which when heated with an excess of hydrobromic acid is converted from the methoxyto the bromo-substituted compound which is heated with excess potassium acetate in acetic acid to replace the bromine atom by an acetate group, which is then saponified with aqueous caustic soda; (3) 2 - methoxy - 5 - diethylamino - methylbenzaldehyde in alcoholic solution is reduced by sodium amalgam and acetic acid to obtain 2 - methoxy - 5 - diethylaminomethylbenzyl alcohol; (4) 4 - methoxy - 3 - dimethylaminomethylbenzaldehyde is reduced to 4-methoxy 3-dimethylaminomethylbenzyl alcohol by the method of (3); (5) 4 - methoxy - 3 - diethylaminomethylbenzyl alcohol is obtained by the method of (4). Dialkylaminomethylbenzaldehydes, e.g. 2 - methoxy - 5 - diethylamino - methylbenzaldehyde and 4 - methoxy - 3 - di - (methyl- or ethyl-) aminomethylbenzaldehyde, are obtained by condensing the corresponding chlormethylbenzaldehydes with the appropriate dialkylamines. The Specification as open to inspection under Sect. 91 comprises also the manufacture of products containing alkyl substituents in the benzene nucleus. This subject-matter does not appear in the Specification as accepted.