Hydrochloric Acid → HCID 12797215, compound

Participants

Reaction Steps

A stirred solution of 3-amino-4-methylbenzoic acid (15.1 g) in dry dimethylformamide (150 ml), containing triethylamine (20.2 g) was treated with n-hexadecanoyl chloride (27.5 g) during 30 minutes. The temperature of the reaction mixture was maintained at 25°-45° C. during the addition by water cooling. The mixture was then stirred for a further hour and was poured into water (1000 ml). The mixture was adjusted to pH 1 by the addition of concentrated hydrochloric acid (strength 0.6% w.v). The solid was collected, was washed with water and was recrystallised from ethanol (1500 ml) to give 3-(n-hexadecanamido)-4-methylbenzoic acid (22.0 g), in the form of a white solid, m.p. 238°-240° C.

Provenance & Evidence