Dodecanoyl chloride → Geranyl laurate

Participants

Reaction Steps

A mixture of geraniol and nerol (approximately 70:30 by weight) in the amount of 50.00 g (0.324 mol) and triethylamine in the amount of 36.08 g (0.357 mol) are combined with 300 mL of toluene. The reaction mixture is heated to reflux and lauroyl chloride in the amount 70.92 g (0.324 mol) is added dropwise over 15 min. After heating for an additional 30 min, the product mixture is cooled to room temperature and filtered. The filtrate is washed three times with 100 mL of saturated NaHCO3, 100 mL of water, and dried over MgSO4. After filtration, the filtrate is concentrated by rotary evaporation followed by Kugelrohr distillation. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13C and 1H NMR.

Provenance & Evidence