Hydrogen Peroxide → 4-{[1,1'-Biphenyl]-4-yl}butanoic acid

Participants

Reaction Steps

To a solution of the above (5.71 g, 10.8 mmol) in 67 ml THF/17 ml water cooled to 0° C. was added a mixture 8.8 ml of 30% H2O2 43.3 mmol of LiOH. The solution was evaporated after 1.5 h, and the resulting material acidified with 10% citric acid. The organic material was extracted with ethyl acetate, washed with water and brine and dried over MgSO4. Filtration and removal of solvent gave a slurry containing the oxazolidinone and crude acid. Addition of ether and a seed crystal of S-4-(phenylmethyl)oxazolidinone followed by cooling to -20, gave a solid precipitate which was removed by filtration. The product acid was further purified by making a dicylohexylamine salt and recrystalizing from ether. The acid was then free based using 5% KHSO4 to give the acid as a crystailne product that could be used without further purification in the next step.

Provenance & Evidence