Potassium Carbonate → Methyl 4-(p-anilinophenoxy)butyrate

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Reaction Steps

A mixture of 198 g. of methyl 4-chlorobutyrate, 269 g. of p-anilinophenol, and 636 g. of anhydrous potassium carbonate, all in 500 ml. of N,N-dimethylformamide was heated at 140° C. while stirring for 4 hours and about 300 ml. of the N,N-dimethylformamide was removed by distillation. The residue was poured into ice water and the resulting mixture was extracted with benzene. The dried benzene extract was chromatographed through a column of neutral alumina and the benzene solvent was stripped from the eluent leaving the product, methyl 4-(p-anilinophenoxy)butyrate, as a dark amber liquid. This ester was sufficiently pure to be used as an antioxidant. Crystallization of the crude ester from ethanol afforded a solid, mp. 40°-41° C.

Provenance & Evidence