Benzyl Alcohol → Benzyl glycidyl ether

Participants

Reaction Steps

A mixture of 50% w/w aqueous potassium hydroxide (30 mL), epichlorohydrin (157 mmol, 20 mL) and tetrabutylammonium bromide (2.35 mmol, 0.75 g) was vigorously stirred at room temperature and cooled in an ice bath. Benzyl alcohol (96.0 mmol, 10 ml) was added dropwise, while maintaining the reaction temperature at about 10° C. by cooling the reaction mixture in an ice bath. The reaction mixture was then allowed to stir at room temperature overnight after which it was poured onto ice/water, and the aqueous phase extracted with diethyl ether. The organic phases were combined and washed with brine to neutrality and dried (Na2SO4). The solution was concentrated under reduced pressure. The residue was purified by flash chromatography (silica, 2-10% ethyl acetate/heptane) to give 14.8 g (94%) of 2-benzyloxymethyl-oxirane.

Provenance & Evidence