Hydrochloric Acid → 4H-Thiopyran-4-one, 3,5-bis[(4-chlorophenyl)methylene]tetrahydro-

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A solution of tetrahydro-4H-thiopyran-4-one (10.0 g, 0.086 mole) and 4-chlorobenzaldehyde (24.0 g, 0.172 mole) in 60 ml ethanol is treated with 6 ml of concentrated HCl and heated at reflux temperature for 2 hours. Upon cooling, 10 g of product is collected. Concentration of the mother liquor and washings to the original volume and adding additional concentrated HCl (4 ml) gives another 12 g of product. The combined crude material, recrystallized from CHCl3 /EtOH gives 15 g of product, m.p. 163°-165°.

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