p-Toluenesulfonic acid → methyl (2R)-2-hydroxy-3-phenylpropanoate

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Reaction Steps

Following the procedure of Cohen (J. Am. Chem. Soc., 1964, 86, 5326), the resultant compound from Example 89 (8.6 g, 52 mmol) was dissolved in dry methanol (250 ml). p-Toluenesulfonic acid (2 g, 10.5 mmol) was added and the solution was refluxed for 2 h. The cooled solution was concentrated in vacuo and the residue was dissolved in ether (400 ml). The ether solution was washed with saturated aqueous NaHCO3 (3×50 ml), water (2×50 ml), 0.1N H2SO4 (1×50 ml), water (1×50 ml), dried over Na2SO4, and concentrated in vacuo to afford a colorless solid. The solid was recrystallized from hexane to provide the title compound as colorless needles (7.7 g, 83%); mp=46°-47° C.

Provenance & Evidence