m-Chloroperbenzoic acid → HCID 18965288, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 5-chloropentyl isopentyl sulfide (1.0 g, 5.39 mmol) in methylene chloride (25 mL), place under nitrogen atmosphere and cool to -20° C. Add, by dropwise addition, a solution of meta-chloroperbenzoic acid (930 mg, 5.39 mmol) in methylene chloride (25 mL). Stir overnight at room temperature. Add additional meta-chloroperbenzoic acid (930 mg). Stir briefly and filter. Treat with aqueous sodium metabisulfite (until negative starch-iodide test) and separate the layers. Wash the organic phase with saturated sodium hydrogen carbonate until basic and dry (MgSO4). Evaporate the solvent in vacuo to yield a yellow oil. Purify by silica gel chromatography (50% ethyl acetate/hexane) to yield 750 mg of 5-chloropentyl isopentyl sulfoxide as a clear oil; MS (CI/CH4) m/z 225(M+1), 189 (M+1-HCl).

Provenance & Evidence