Hydroxyphenylacetic acid → 4-Hydroxy-3-nitrophenylacetic acid

Participants

Reaction Steps

A solution of nitric acid (24.5 ml, 398 mmol) in acetic acid (20 ml) was slowly added dropwise under cooling with ice-bath to a solution of (4-hydroxyphenyl)acetic acid (50.4 g, 330 mmol) in acetic acid (230 ml) such that the temperature of the reaction solution did not exceed 10° C. After the reaction solution was stirred for 2 hours, water (1 L) was added dropwise thereto and the precipitated crystals were collected by filtration. The resultant crystals were washed with water and dried, whereby (4-hydroxy-3-nitrophenyl)acetic acid (49 g) was obtained as crystals with a mp of 144 to 146° C.

Provenance & Evidence