Benzyl Bromide → Hexaethylene Glycol Monobenzyl Ether

Participants

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). Aqueous sodium chloride solution (15% w/w, 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). LC retention time 2.50 mins. Mass spectrum m/z 390 [MNH4+]

Provenance & Evidence