Benzaldehyde → 1-Phenyl-2-(4-methylthiophenyl)-1-buten-3-one

Participants

Reaction Steps

A solution of 1-(4-methylthiophenyl)-2-propanone [G. Y. Lesher, U.S. Pat. No. 4,517,192, May 14, 1985; L. M. Werfel et al, J. Med. Chem., 29, 924-36 (1986)] (11.2 g, 0.062 mol) and benzaldehyde (6.6 g, 0.062 mol) in benzene (75 ml) containing piperidine (200 mg) was heated at reflux for 24 hours. After cooling, the solvent was removed and the residue was purified by chromatography on silica gel using mixtures of ethyl acetate and toluene to give the ketone. This material was recrystallized from ethyl acetate and hexane to give 14 g (82%) of pure ketone as a crystalline solid: mp 91°-93° C. Anal. Calc'd. for C17H16OS (268.38): C, 76.08; H, 6.01; S, 11.95. Found: C, 76.15; H, 6.08; S, 11.79.

Provenance & Evidence