4-METHOXY-3-METHYLBENZYL CHLORIDE

67-72-1

114787-91-6

60736-71-2

The general procedure for the synthesis of 4-methoxy-3-methylbenzyl chloride from hexachloroethane and 4-methoxy-3-methylbenzyl alcohol is as follows: to a stirred solution of 4-methoxy-3-methylbenzyl alcohol (2.31 g, 15.18 mmol, 1 eq.) in anhydrous methylene chloride (50 mL, 0.3 M) was added hexachloroethane (3.59 g, 15.18 mmol, 1 eq.) and triphenylphosphine (3.98 g, 15.18 mmol, 1 eq.) in sequence. ) and triphenylphosphine (3.98 g, 15.18 mmol, 1 eq.). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the mixture was transferred to a partition funnel, washed sequentially with water and brine, the organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 30% ethyl acetate/hexane) to afford the target product 4-methoxy-3-methylbenzyl chloride (2.59 g, 100% yield). The structure of the product was confirmed by 1H NMR (CDCl3, 400 MHz): δ 7.16 (m, 2H), 6.76 (d, 1H, J = 8.10 Hz), 4.52 (s, 2H), 3.81 (s, 3H), 2.19 (s, 3H).