Benzyl Alcohol → Benzyl glycidyl ether

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.

1. temperaturecooled in an ice bath
2. temperaturewhile maintaining the reaction temperature at about 10° C.
3. temperatureby cooling the reaction mixture in an ice bath
4. stirringto stir at room temperature overnight after which it
5. additionwas poured onto ice/water
6. extractionthe aqueous phase extracted with diethyl ether
7. washwashed with brine to neutrality
8. dry with materialdried (Na2SO4)
9. concentrationThe solution was concentrated under reduced pressure
10. customThe residue was purified by flash chromatography (silica, 2-10% ethyl acetate/heptane)

ORD record

ord-55726831cc934674ae5b0c2d357ff1da

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642603B2