Chloroform → Benzyl (s)-hexahydromandelate

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A flask was charged with (S)-hexahydromandelic acid (0.88 g, 5.56 mmol), Bu4NI (0.4 g, 1.1 mmol) and KOH (11.1 mL, 5.56 mmol, 0.5 M in water). 11 mL of chloroform was added followed by benzyl bromide (0.66 mL, 5.56 mmol). The mixture was refluxed for 5 h then cooled and diluted with 100 ml CH2Cl2. The layers were separated and the organic was dried and concentrated. Flash Chromatography (7/1 hexane/EtOAc) gave the desired product. RF: 0.37 (4:1 v/v hexanes/EtOAc); 1H NMR (300 MHz, CDCl3) δ1.11-1.38 (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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