4-Hydroxybenzoic Acid → 4-(Hexanoyloxy)benzoic acid

Participants

Reaction Steps

10 g 4-hydroxybenzoic acid was dissolved in 50 ml dry pyridine. The solution was then externally cooled with ice water while 10.5 g hexanoyl chloride was added dropwise. After the resultant mixture had been further stirred overnight at room temperature, it was poured in 300 ml 3-N dilute hydrochloric acid. White precipitate was taken up by filtration. By recrystallizing the white precipitate in a mixed solvent of methanol/water (3:2), 14.8 g 4-hexanoyloxybenzoic acid was obtained in 87% yield based upon the amount of the hydroxybenzoic acid.

Provenance & Evidence