Acetic Acid → N-acetyl-N-(2-acetyloxybenzyl)-2-phenoxyaniline

In 30 ml of methanol were dissolved 1.74 g of 2-acetoxybenzaldehyde and 1.85 g of 2-phenoxyaniline, and after stirring at room temperature for an hour, 3.00 g of sodium borohydride was added, followed by stirring at the same temperature for 30 minutes. To the reaction solution was added dropwise an aqueous acetic acid solution (3.0 ml of acetic acid and 60 ml of water), and after stirring at room temperature for 10 minutes, the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure. A solution of the residue and 4 ml of triethylamine in 50 ml of methylene chloride was cooled to 0° C., and 2.00 ml of acetyl chloride was added dropwise with stirring, followed by stirring at room temperature for 20 minutes. The reaction mixture 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 to give a crude N-acetyl-N-(2-acetyloxybenzyl)-2-phenoxyaniline.