[Synthesis]
At 0°C, 4 g (23.4 mmol) of 3-(chloromethyl)benzoic acid was dissolved in 250 g of anhydrous ether. Subsequently, 30 ml of lithium methyl solution was slowly added dropwise to this solution. After the dropwise addition was completed, the reaction mixture was continued to be stirred at 0°C for 30 minutes. Upon completion of the reaction, the reaction was quenched by the slow addition of water and the mixture was acidified with hydrochloric acid. The organic phase was separated, washed several times with water and dried with anhydrous magnesium sulfate. The organic phase was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent ethyl acetate:heptane (5:95, v/v). Finally, 2.7 g of 3'-chloromethylacetophenone was obtained in 69% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (3H, s), 4.63 (2H, s), 7.44-7.50 (1H, t), 7.59-7.62 (1H, d, J = 7.6 Hz), 7.89-7.93 (1H, d, J = 6.5 Hz), 7.97 (1H, s). |