m-Chloroperbenzoic acid → 1,2-Epoxy-1-(4-nonylphenyl)-hexane

Participants

Reaction Steps

6.76 g of m-chloroperbenzoic acid (90% content) in 100 ml of dichloromethane are added to a solution of 6.32 g of 1-(4-nonylphenyl)-hex-1-ene (mixture of cis- and trans-isomers) from the preceding stage in 150 ml of dichloromethane while cooling to 0°-5°, and the whole is stirred for 20 hours at 20°. The rection mixture is washed in succession with 10% strength (w/v) sodium sulphite solution, 5% strength (w/v) sodium carbonate solution and 3 portions of water, dried over sodium sulphate and concentrated by evaporation. Chromatography of the residue on silica gel with hexane/ethyl acetate (19:1) yields in succession the trans-[1(RS),2(RS)-] and the cis-[1(RS),2(SR)-] -isomer in the form of colourless oils.

Provenance & Evidence