Chloroacetyl chloride → HCID 19959496, compound

Participants

Reaction Steps

32.6 g (0.181 mol) of chloroacetyl chloride are added, followed within 15 minutes by 20 g (0.121 mol) of N-(3-methoxyphenyl)acetamide, to a solution of 64.6 g (0.484 mol) of aluminum chloride in 100 ml of 1,2-dichloroethane at 0° C. under argon. The temperature rises to 10° C. during this. The mixture is then slowly warmed to room temperature and stirred overnight. The brown mixture is added to ice-water, and ethyl acetate is added. After vigorous stirring, N-(3-methoxy-4-chloroacetylphenyl)acetamide precipitates and is filtered off with suction and dried under higher vacuum. The resulting solid is introduced into 140 ml of ethanol and, after addition of 13.2 g (0.154 mol) of sodium acetate, heated under reflux overnight. Cooling is followed by addition of water, and the ethanol is stripped off in a rotary evaporator. The precipitated solid is filtered off with suction on a frit and dried. 9.35 g (40% of theory) of the product result as a solid with a pale reddish color.

Provenance & Evidence