1-Dodecanol → 5-Dodecyloxy-2-furoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 30.0 g (0.157 mole) of 5-bromofuroic acid, 29.4 g (0.157 mole) of dodecanol and 500 ml of pyridine is flushed with nitrogen and stirred at room temperature after which 7.55 g (0.314 mole) of sodium hydride is added. The mixture is heated to 100° C for 20 hours, then refluxed 1 hour after which 2.0 g of cuprous chloride is added. The mixture is refluxed with stirring under nitrogen for 20 hours, then poured into an ice-water-hydrochloric acid mixture with stirring and filtered. The resulting oily precipitate is extracted into ether, washed with 5% hydrochloric acid solution, water and salt water, dried over sodium sulfate, filtered, and evaporated on a steam bath replacing the ether with hexane. The solid obtained is recrystallized from methanol to give 5-dodecyloxy-2-furoic acid, M.P. 122°-123° C.

Provenance & Evidence