4,4'-Thiobis(2-tert-butyl-6-methylphenol) → HCID 178526895, compound

Participants

Reaction Steps

3-(2-Nitroimidazolyl)-2-hydroxy-1-butene (11.83 gms, m.p. 90°-92° C., prepared by refluxing a mixture of azomycin, 1,3-butadiene monoxide and anhydrous potassium carbonate in ethanol for 5 hours) is stirred overnight in dichloroethane with m-chloroperbenzoic acid in the presence of 3-tert-butyl-4-hydroxy-5-methylphenyl sulfide and after stirring the reaction mixture is refluxed for 1 hour. The mixture is washed with saturated sodium carbonate solution and the aqueous phase was extracted with chloroform. The combined dichloroethane and chloroform extracts are concentrated to a small volume and the product is purified by column chromatography, in which silica gel is the stationary phase and a mixture of chloroform (90%) and ethanol (10%) the eluent. The product is crystallised from ethanol as a pale yellow solid of m.p. 134°-136° C. Yield 33%.

Provenance & Evidence