64-19-7

498-02-2

54771-60-7

General procedure for the synthesis of 1-(4-acetoxy-3-methoxyphenyl)ethanone from glacial acetic acid and vanillylacetophenone: reference to Example 1. Preparation of intermediate (1): 4-acetyl-2-methoxyphenyl acetate (1). 500 mg (3 mM) of acetylisopropyl ketone was dissolved in 20 mL of THF and 0.5 mL of pyridine and 0.6 mL of anhydrous acetic acid were added. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the product was extracted with diethyl ether and the organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with hexane:ethyl acetate (4:1) as mobile phase to give 4-acetyl-2-methoxyphenyl acetate (1; 625 mg) as white solid. Melting point: 58.7 °C; 1H NMR (CDCl3): δ 7.60 (d, 1H, J = 1.8 Hz, H-3), 7.55 (dd, 1H, J = 1.8, 8.2 Hz, H-5), 7.12 (d, 1H, J = 8.2 Hz, H-6), 3.89 (s, 3H, OCH3), 2.59 (s, 3H, OCOCH3) and 2.33 (s, 3H, COCH3).