Water → (S)-1-(3-Chlorophenyl)ethane-1,2-diol

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AD mix alpha (86.0 g) was added to a stirred mixture of tert-BuOH (300 ml) and H2O (300 ml), mixture was stirred for 15 min at RT, than cooled to 0° C. 3-Chlorostyrene (8.51 g, 0.061 mol) was added over 15 min. The mixture was stirred at 0° C. for 48 h. The reaction was quenched by adding 10% aq. sodium sulfite (120 ml) followed by addition of EtOAc (200 ml). The layers were separated and the aqueous layer was extracted with EtOAc (200 ml). The combined organic layers were washed with 0.4 M H2SO4 in saturated Na2SO4 (100 ml), followed by drying over Na2SO4. The solvent was evaporated, the residue was separated on SiO2 (70 g) (CHCl3-MeOH 0 to 10%). Colorless oil, 9.83 g (0.057 mol, 93%). 1H NMR (300 MHz, DMSO) δ 7.20-7.40 (m, 4H), 5.39 (d, J=4.6 Hz, 1H), 4.76 (t, J=5.8 Hz, 1H), 4.54 (q, 4.9=Hz, 1H), 3.43 (m, 2H)

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