Diethyl Ether → 1-Phenylethanol, (R)-

Participants

Reaction Conditions

Reaction Steps

Anhydrous zinc bromide (11.37 g) was charged to a dry, stirred 250 ml flask filled with nitrogen. Dried diethylether (75 ml) was added and the slurry heated to reflux until a homogenous solution. A 3molar ethereal solution of phenylmagnesium bromide (33.3 ml) was slowly added. Solvent was distilled from the reaction mixture at ambient pressure, whilst maintaining a constant volume by addition of toluene until a distillate temperature of 110° C. was reached. The hot slurry was screened under a nitrogen atmosphere using an in-line sintered glass filter. The filtrates were received into a dry, stirred 250 ml flask and cooled to −5° C. D(+) diethyinorephedrine (0.64 g) was added and the acetaldehyde (2.2 g) in toluene (5 ml) charged from a dropping funnel. The reaction mixture was warmed to ambient temperature, stirred for a total of 12 hours, then cooled on an ice bath and quenched by addition of dilute hydrochloric acid. The organic layer was separated, washed with an equal volume of water and concentrated to yield a crude product (4.62 g). This was further purified by chromatography to give 3.86 g (R)phenylethanol of 17% ee, measured by chiral GC. The product was identified by gas chromatographic comparison with authenticated material.

Provenance & Evidence