tert-Butyl hydroperoxide → HCID 57305581, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(3-oxo-1E-propenyl)benzoate (0.67 g, 3.52 mmol) and 10 ml of methanol was added dropwise to 0.58 ml of 70% 1,1-dimethylethylhydroperoxide (4.2 mmol) in 5 ml of methanol. The pH was maintained at pH 8.0-8.5 throughout with 1N sodium hydroxide. The mixture was stirred at about 35° C. for 1.5 hrs. The reaction mixture was poured into ether/water and the ether layer was washed 3× with water and 1× with brine, dried over sodium sulfate, and concentrated. Flash chromatography using 10:1 followed by 2:1 hexane/ethyl acetate provided the product, methyl trans-3-(3-formyloxiranyl)benzoate as the pure trans epoxide.

Provenance & Evidence