m-Chloroperbenzoic acid → 2-(Diphenylmethyl)oxirane

Participants

Reaction Steps

A flask was charged with 3,3-diphenylpropene (5.1 g, 26.3 mmol) in 100 ml CH2Cl2. It was followed by portionwise addition of mCPBA (9.1 g, 70% purity, 52.6 mmol) at 0° C. The mixture was stirred at room temperature for 24 h and the reaction was then quenched with 30 ml 1M Na2SO3. The aqueous layer was extracted with CH2Cl2 (2×100 ml). The combined organic phases were washed in turn with saturated NaHCO3, brine, and then dried over anhydrous Na2SO4. Purification by flash chromatography (Hexane/ether=9:1) gave pure 2-benzhydryl-oxirane, 4.7 g (85%).

Provenance & Evidence