Hydrochloric Acid → HCID 54710939, compound

Participants

Reaction Steps

A mixture of the monosodium salt of 4-hydroxy-6-methyl-2-pyrone (29.6 g., 0.200 mol), p-chlorophenyl p-toluenethiolsulfonate (59.8 g., 0.200 mol), and 2B absolute ethanol (500 ml.) was heated at reflux with stirring for 6.5 hours. The ethanol was removed by distillation in vacuo and the residue triturated with water (300 ml.). The crude product was removed by filtration, 53.0 g. (m. 166°-177°C., 91% yield); after recrystallization from ethanol, 36.4 g., m. 175°-180°C., 68% yield. A second recrystallization produced the pure product, 18.0 g., m 181°-182°C., 34 percent yield. The aqueous filtrate was acidified with dilute HCl producing 21.8 g. (70 percent yield) of the by-product p-toluenesulfinic acid, m. 87°-89°C.

Provenance & Evidence