Benzyl Bromide → Hexaethylene Glycol Monobenzyl Ether

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium hydride (50% dispersion in mineral oil, 2.55 g) in tetrahydrofuran (100 ml) was added hexaethylene glycol (25 g). The reaction mixture was stirred at 5-15° C. for 10 minutes, then benzyl bromide (16.66 g) was added. The suspension was allowed to stand at 20° C. for 72 hours then the reaction mixture was diluted with water (250 ml) and extracted with cyclohexane (250+125 ml). 15% w/w. Aqueous sodium chloride solution (300 ml) was added to the aqueous phase and the resulting solution was extracted with ethyl acetate (3×250 ml). The combined ethyl acetate extracts were concentrated in vacuo to give the title compound as an orange oil (18.68 g).

Provenance & Evidence