Chloroacetyl chloride → Benzenepropanoic acid, 4-(chloroacetyl)-, methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 50 g of methyl 3-phenylpropionate, 51.6 g of chloroacetyl chloride and 250 ml of dichloromethane was cooled to 0° C. The mixture was stirred at 0° to 10° C. and 122 g of aluminum chloride was added gradually into the mixture. The reaction mixture was then stirred at a room temperature for 2 hours. The reaction mixture was allowed to stand overnight, then the reaction mixture was poured into a mixture of ice-concentrated hydrochloric acid and was extracted with chloroform. The chloroform layer was washed with water, dried then chloroform was removed from the reaction mixture by distillation. The residue thus obtained was crystallized by adding isopropyl ether, and the crystals formed were collected by filtration, then recrystallized from ethanol to obtain 53.4 g of methyl 3-(4-chloroacetylphenyl)propionate in the form of needle-like crystals.

Provenance & Evidence