Benzyl Bromide → Benzyl (s)-hexahydromandelate

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A solution of 500 mg (3.2 mmol) of (S)-hexahydromandelic acid and 238 mg (0.6 mmol) of tetrabutylammonium iodide in 6.5 mL of CHCl3 was treated with 6.5 mL of 0.5 N KOH and 0.38 mL (3.2 mmol)of benzyl bromide then stirred at 70° C. for 1.5 h. The reaction was cooled to rt and the layers were separated. The aqueous phase was extracted with 2×50 mL CH2Cl2. The organic phases were combined, dried over Na2SO4 and concentrated. Flash chromatography using 17:3 v/v hexanes/EtOAc as the eluant afforded 616 mg (77%) of the title compound: RF: 0.37 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 1.11-1.38 (m, 11H), 2.65 (d, J=6.3 Hz, 1H), 4.06 (dd, J=6.3, 3.5 Hz, 1H), 5.22 (s, 2H), 7.30-7.39 (m, 5H).

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