Hexamethylenetetramine → 4-(Aminoacetyl)phenoxyacetic acid hydrochloride

Participants

Reaction Steps

A solution of 4-(bromoacetyl)phenoxyacetic acid (26g.) in chloroform (150ml.) was stirred as hexamine (14g.) was added. The mixture was stirred at room temperature for 3 days and then filtered. The solid was suspended in ethanol (250ml.), concentrated hydrochloric acid (50ml.) was added and the mixture stirred at room temperature for 18 hours. The mixture was then filtered and the filtrate diluted with diethyl ether (1,500ml.). The solid so produced was filtered off, washed with a mixture of ethanol and diethyl ether to give 4-(aminoacetyl)phenoxyacetic acid hydrochloride, m.p. > 250° C. N.m.r. δ 7.0-7.14, 7.92-8.06 each 2H (aromatic protons), 4.5 (2H, N⊕H3CH2CO) and 4.81 (2H, --OCH2.COOH).

Provenance & Evidence