m-Chloroperbenzoic acid → HCID 86745361, compound

Participants

Reaction Steps

7.8 g of m-chloroperbenzoic acid (about 50% pure) are added to a solution of 6 g of methyl 2-(2-phenylethenyl)phenylacetate (E/Z=3:1) in 50 ml of methylene chloride. The reaction mixture is refluxed for 12 hours and then the precipitate is filtered off with suction and the filtrate is washed twice with saturated sodium bicarbonate solution and water. The isolated organic phase is dried over sodium sulfate and concentrated, and the residue is recrystallized from methyl tert-butyl ether. 3.1 g (48%) of methyl trans-2-(3-phenyl-2-oxiranyl)phenylacetate are obtained of melting point 118°-119° C. Chromatography of the mother liquor on silica gel (6:1 ethyl acetate/n-hexane) yields 2.8 g (44%) of methyl 2-(3-phenyl-2-oxiranyl)phenylacetate as a 1:1 cis/trans mixture.

Provenance & Evidence