Acetyl chloride → 2-Phenoxyacetanilide

Participants

Reaction Steps

To a solution of 28.5 g of 2-phenoxyaniline and 25.8 ml of triethylamine in 250 ml of methylene chloride was added dropwise 11.5 ml of acetyl chloride under ice-cooling. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 33.7 g of N-acetyl-2-phenoxyaniline.

Provenance & Evidence