4-(Aminomethyl)Benzoic Acid → [4-(Aminomethyl)phenyl]methanol

Participants

Reaction Steps

A solution of 4-aminomethyl-benzoic acid (0.20 g) in 20 mL diethyl ether was cooled to 0° C. Lithium aluminum hydride (0.19 g) was added in portions to the stirring carboxylic acid solution. The resulting slurry was stirred for 20 h and then cooled to 0 C. The mixture was carefully quenched by the sequential addition of 0.2 mL of water followed by 0.2 mL of 3 N sodium hydroxide followed by 0.6 mL of more water. The mixture was stirred for 15 min, then filtered to remove the aluminum salts. The filtrate was collected and the volatile material was evaporated to give 150 mg of (4-aminomethyl-phenyl)-methanol.

Provenance & Evidence