Hydrochloric Acid → HCID 54729787, compound

Participants

Reaction Conditions

Reaction Steps

4-Hydroxy-3-mercapto-6-methyl-2-pyrone (49.5 g., 0.313 mole) and o-fluorobenzyl chloride (45.3 g., 0.313 mole) were dissolved in pyridine (250 ml.). The temperature rose from 20° to 43°C. The solution was heated at 90°C. for two hours, cooled and poured over ice and concd. hydrochloric acid (500 ml.). This mixture was extracted with methylene chloride. The extract was dried (MgSO4) and evaporated to dryness, leaving an oily residue (80 g.) which is dissolved in hot benzene. Hexane was added to this hot benzene solution and an oil separated. The solution was decanted off. This was repeated until a solid separated. The mixture was cooled and filtered, giving 38.0 g. (46 percent) of the desired product. Recrystallization from benzene gave the pure product as a pale yellow solid, m.p. 123°-125°C.

Provenance & Evidence