Hydrochloric Acid → Ethyl (4-acetylphenyl)acetate

Participants

Reaction Steps

To a solution of ethyl 2-phenylacetate (A-1) (50.9 g, 305 mmol) in CS2 (220 mL) was added AlCl3 (93.6 g, 702 mmol) at 0˜10° C. over 10 min. After addition, acetyl chloride (30.5 mL, 427 mmol) was added at 0˜10° C. over 10 min. After addition, the reaction mixture was slowly heated to reflux overnight, then poured into ice-cooled 5N HCl solution (600 mL), extracted with EA (200 mL×3). The combined organic phase was washed with water (200 mL), sat. NaHCO3 (200 mL) and brine (200 mL), dried over Na2SO4, concentrated to afford a brown oil. Recrystallized with PE/acetone (150 mL/20 mL) in refrigerator to afford A-2 as a yellow crystal solid (13.8 g, 19%).

Provenance & Evidence