3-Phenyllactic acid, (S)- → (S)-a-Hydroxy-cyclohexanepropanoic acid

Participants

Reaction Steps

To a solution of (S)-3-phenyllactic acid (20g) in ethanol (250mL) was added 5% rhodium on alumina (2.5 g), and the reaction was shaken under 4atm H2 for 24 h. The reaction was filtered, and concentrated to give product as a white solid (≈20 g). 1H NMR (300 MHz, CDCl3) δ0.86-1.07 (m, 2H), 1.08-1.39 (m, 3H), 1.54-1.91 (m, 9H), 4.33 (dd, J=9.3, 3.6 Hz, 1H). MS(CI/NH3) m/e: (M+NH4)+ 190.

Provenance & Evidence