Water → 2-Oxo-4-phenylbutyric acid

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.

1. filtrationfiltered
2. washThe crude cake was rinsed with 20 ml of Et2O
3. customto give a pale yellow solid, which
4. extractionextracted with Et2O
5. extractionThe neutral impurities in the filtrate were extracted with Et2O
6. waitany acidic material left in the acidified filtrate (pH=2 by adding HCl)
7. extractionwas extracted with Et2O (3×30 ml)

ORD record

ord-b34e99d69bae43ef99b39b074603ddd3

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04492798