Acetyl chloride → N-[5-(Hydroxymethyl)-2-methylphenyl]acetamide

Participants

Reaction Steps

The solution of 11.3 g of (3-amino-4-methylphenyl)methanol in 500 ml of chloroform is cooled to 0° C. with stirring and admixed with 13.4 ml of triethylamine. 6.03 ml of acetyl chloride are slowly added dropwise. Subsequently, the mixture is stirred at 0° C. over 2 hours. The reaction mixture is poured onto water (1 l) and extracted with dichloromethane (2×350 ml). The organic phases are washed with brine (350 ml), dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a slightly brownish solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.10 (1:2 dichloromethane-diethyl ether); Rt=2.14.

Provenance & Evidence