[H-].[Na+].CN(C=O)C.[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1.[CH3:18][O:19][C:20](=O)[O:21]C>O>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][C:20]([O:19][CH3:18])=[O:21])=[CH:11][CH:10]=1To a 250 mL RB flask fitted with magnetic stirrer was charged with sodium hydride (3.5 g, 147 mmol). At 0 deg C., 100 mL of DMF was added slowly with stirring. To the stirred solvent were added 1-(4-hydroxyphenyl)ethanone (5 g, 36 mmol) and dimethylcarbonate (15.5 g, 170 mmol), stirred at room temperature overnight. The RM was poured into water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water (50 mL) and saturated brine solution (50 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as elutants. The product was obtained as pale yellow oil (3.4 g, yield: 47.66%). MS (ESI, 120 eV): m/z=195 (M+H)+; 1H NMR (300 MHz, CDCl3): δ 7.79-7.82 (d, 2H), 6.81-6.84 (d, 2H), 6.21 (br s, 1H), 3.90 (s, 2H), 3.69 (s, 3H).
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