2-[(4-Methylphenyl)sulfonyl]ethanol

699-02-5

22381-54-0

General procedure for the synthesis of 2-(p-toluenesulfonyl)ethanol from 4-methylphenylethanol: To a mixture of acetic acid (50 mL) and water (50 mL) of compound 2 (20 g, 0.119 mol) was added slowly and dropwise over a period of one-half hour 30% hydrogen peroxide (36.5 mL) under ice-bath conditions. Subsequently, the reaction mixture was refluxed for 20 minutes and then cooled to room temperature. Sodium bicarbonate was added to the reaction mixture to neutralize the solution, followed by ethyl acetate for extraction. The organic layer was separated, washed sequentially with saturated saline and deionized water, and finally concentrated under reduced pressure to give 22.9 g (96.3% yield) of target product 3 as a white solid. The structure of the product was confirmed by 1H NMR (270 MHz, CDCl3) and 13C NMR (67.9 MHz, CDCl3): 1H NMR (270 MHz, CDCl3) δ 2.46 (s, 3H), 3.33 (t, J = 5.4 Hz, 2H), 3.99 (t, J = 5.4 Hz, 2H), 7.39 (d, J = 8.0 Hz, 2H), 7.81 (d, J = 8.3 Hz, 2H); 13C NMR (67.9 MHz, CDCl3) δ 21.7, 56.4, 58.3, 128.0, 130.1, 136.0, 145.2.