119650-44-1

106116-42-1

119650-44-1

General procedure for the synthesis of (3-methoxy-5-methylphenyl)methanol from 1-(bromomethyl)-3-methoxy-5-methylbenzene: To a solution of 1-(bromomethyl)-3-methoxy-5-methylbenzene (2.14 g) in acetone (80 mL) was added sodium bicarbonate (1.05 g) and water (50 mL), the mixture was heated and refluxed for 18 hours. Upon completion of the reaction, the reaction mixture was extracted with ethyl acetate, the organic layers were combined and washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to afford the target compound as a yellow oil (1.22 g).1H NMR (400 MHz, CDCl3) δ 2.35 (3H, s), 3.82 (3H, s), 4.64 (2H, s), 6.68 (1H, s), 6.75 (1H, s), 6.79 (1H, s).