Acetic Acid → 5-Tetradecylthio-2-furoic acid

Participants

Reaction Steps

A mixture of 20.1 g (0.011 mole) of 5-bromofuroic acid, 24.2 g (0.011 mole) of tetradecanethiol in 800 ml of dimethylformamide and 8.5 g (0.021 mole) of sodium hydride is heated on a steam bath overnight then refluxed for one-half hour. The mixture is then cooled, acidified with acetic acid and extracted with ether-water. The ether layer is washed with water and salt water, dried over sodium sulfate and filtered. The filtrate is evaporated to dryness, and the remaining solid is recrystallized from hexane and from methanol to give 5-tetradecylthio-2-furoic acid, M.P. 84°-86° C.

Provenance & Evidence