To a solution of 2',3',4'-trihydroxyacetophenone (1.66 g, 10 mmol) in acetone (50 mL) was added potassium carbonate (11 g) and dimethyl sulfate (6 mL, 30 mmol). The reaction was stirred at 45 °C for 17 h. The reaction was terminated by the addition of water. The reaction mixture was filtered, neutralized with 1 M HCl and then extracted with dichloromethane (200 mL). The organic layer was washed with brine (150 mL) and the crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate, 5:1). Yield: 1.85 g (88%).1H NMR (CDCl3, 300 MHz) δ 7.50 (d, J = 8.8 Hz, 1H), 6.68 (d, J = 8.8 Hz, 1H), 3.94 (s, 3H), 3.89 (s, 3H), 3.85 (s, 3H), 2.58 (s, 3H) ppm.13C NMR ( CDCl3, 75 MHz) δ 198.01, 157.44, 154.30, 128.99, 125.78, 125.57, 106.99, 61.30, 60.80, 56.06, 30.97 ppm. Pharm. Bull. 1984, 32, 3354-3360.
