Hydrochloric Acid → (2S)-2-benzoxy-4-methylpentanoic acid

Participants

Reaction Steps

To the above methyl (2S)-2-benzoxy-4-methylpentanoate (0.69 g, 2.92 mmol) in MeOH/H2O (5 mL/1 mL) was added LiOH.H2O (0.28 g, 11.7 mmol) and 30% H2O2 (0.3 mL, 11.7 mmol). After stirring the reaction mixture for 24 h, the mixture was treated with 1N HCl (pH=3) and the methanol was removed in vacuo. The aqueous layer was extracted with EA (4×15 mL). The combined organic layers were washed with 1N HC (2×10 mL), sat. NaCl (2×10 mL), dried (MgSO4), filtered and concentrated. (2S)-2-benzoxy-4-methylpentanoic acid was isolated as a colorless oil (0.65 g, 100%): 1H NMR (CDCl3, 300 MHz) 67 0.82-1.60 (m, 6 H), 1.53-1.62 (m, 1 H), 1.73-1.90 (m, 2 H), 3.99-4.50 (m, 1 H), 4.46 (d, 1 H, J=12.0 Hz), 4.72 (d, 1 H, J=12.0 Hz) 7.10-7.26 (m, 5 H) ppm.

Provenance & Evidence