Hydrochloric Acid → 2-(2-Methylphenoxymethyl)-phenylacetic acid methyl ester

Participants

Reaction Steps

5.12 g of o-cresol and 7.2. g of pulverized potash in 30 ml of acetonitrile are preheated to 60° C. and a solution of 11.06 g of 2-(bromomethyl)-phenylacetic acid methyl ester in 35 ml of acetonitrile is added dropwise over a period of 8 minutes. The reaction mixture is then stirred for 4 minutes and immediately poured onto ice-water and weakly acidified with 2N hydrochloric acid. The aqueous solution is extracted exhaustively with ethyl acetate and the combined organic phases are washed with water, dried over sodium sulfate, filtered and concentrated by evaporation. Chromatography on silica gel with hexane/ethyl acetate (9:1) yields pure 2-(2-methylphenoxymethyl)-phenylacetic acid methyl ester in the form of a pale yellow oil.

Provenance & Evidence