Water → 2-Oxo-4-phenylbutyric acid

Participants

Reaction Steps

9.25 g (50 mmoles) of phenethyl bromide, 30 ml of t-BuOH, 700 mg (~2 mmoles) of Co2 (CO)8, 80 ml of H2O, 4.8 g (200 mmoles) of LiOH were stirred in a 300 ml autoclave for 24 hours at 70° C. and under 300 psig CO pressure. The reaction mixture was cooled to room temperature, then filtered. The crude cake was rinsed with 20 ml of Et2O to give a pale yellow solid, which was acidified in cooled HCl solution (check by pH paper) and extracted with Et2O. The neutral impurities in the filtrate were extracted with Et2O and discarded; any acidic material left in the acidified filtrate (pH=2 by adding HCl) was extracted with Et2O (3×30 ml). Approximately 74% isolated yield of benzylpyruvic acid identified by both 1H NMR and 13C NMR was obtained from the combined Et2O solution.

Provenance & Evidence