4-tert-Butylphenol → 4-tert-Butylphenyl glycidyl ether, (+)-

Participants

Reaction Conditions

Reaction Steps

To a mixture of (R)-epichlorohydrin (12.4 g, 134 mmol) and 4-tert-butylphenol (10.0 g, 66.8 mmol) in acetone (50 ml) was added potassium carbonate (9.24 g, 66.8 mmol). The mixture was stirred at 45° C. for 96 hours. The reaction mixture was then concentrated to remove acetone. The residue was partitioned between ethyl acetate and water and extracted twice with ethyl acetate. The organic phases were combined and washed with water, brine, dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by flash chromatography (silica, methylene chloride/heptane) to give 9.18 g (67%) of (S)-2-(4-tert-butyl-phenoxymethyl)oxirane.

Provenance & Evidence