Benzoic Acid → 6-Octen-1-ol, 3,7-dimethyl-, 1-benzoate

Participants

Reaction Steps

A mixture of benzoic acid (14.6 g, 0.12 mol) and citronellol (15.6 g, 0.1 mol) in tetrahydrofuran (THF) was heated on a water bath for 4 hours after the addition of concentrated sulfuric acid. The reaction was monitored by thin layer chromatography (TLC), and when the reaction was over, the reaction mixture was quenched over ice/water, extracted with THF or methylene chloride, washed with 5% sodium hydrogen carbonate, and dried over magnesium sulfate. The reaction mixture was concentrated under vacuum and purified by open column chromatography to yield 4.95 g (yield: 19%) of a product having the following physical properties.

Provenance & Evidence