1-Butanol → Butyl Glycolate

Participants

Reaction Steps

To 101 g (1.5 moles) of butyl alcohol containing 5 g of ρ-toluene sulfonic acid in 325 ml of benzene at reflux was added dropwise 150 g (ca. 1.5 moles acid) of 70% glycolic acid. The flask was equipped with a Dean-Stark trap to collect the 30% of water from the aqueous glycolic acid mixture and to collect the 27 g (1.5 moles) of water liberated during the reaction--a total of ca. 68 ml. The benzene solution of the product was water washed and dried over anhydrous sodium sulfate. The benzene was stripped off on a rotary evaporator. A short pass distillation at reduced pressure produced a good grade butyl glycolate. The structure was established by infrared and nuclear magnetic resonance spectroscopy.

Provenance & Evidence