[C:1]1([C:7]([OH:12])([CH3:11])[CH2:8][CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:20][C:19]1[CH:21]=[CH:22][C:16]([S:13]([O:10][CH2:9][CH2:8][C:7]([OH:12])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH3:11])(=[O:15])=[O:14])=[CH:17][CH:18]=1To a solution of 3-phenylbutane-1,3-diol (68 g, 0.41 mol) in dry CH2Cl2 (500 mL) was added dropwise a solution of TsCl (78 g, 0.41 mol) and triethylamine (71 mL, 0.45 mol) in dry CH2Cl2 (500 mL) at 0° C. The mixture was stirred overnight. The mixture was poured into water and separated. The aqueous layer was extracted with CH2Cl2 (200 mL) twice. The organic layer was combined, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by column chromatography to give 3-hydroxy-3-phenylbutyl 4-methylbenzenesulfonate (62 g, 42%). 1H NMR (400 MHz, CDCl3): δ=1.55 (s, 3H), 1.93 (w, 1H), 2.19˜2.24 (q, 2H), 2.45 (s, 3H), 3.87˜4.01 (m, 1H), 4.09˜4.16 (m, 1H), 7.19˜7.34 (m, 7H), 7.68˜7.76 (d, 2H).
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