Benzyl Bromide → p-(Benzyloxy)phenethyl alcohol

Participants

Reaction Steps

NaH (1.42 g of 60% in oil, 0.036 mol) was washed 2×5 ml hexane and then suspended in tetrahydrofuran (20 ml). 4-Hydroxyphenethyl alcohol (5.0 g, 0.036 mol) was added portionwise and the mixture stirred for 20 minutes to assure complete conversion to the sodium salt. Benzyl bromide (4.2 ml, 1 equivalent) was added and the resulting mixture refluxed for 4 hours, then poured into 50 ml H2O and extracted 3×50 ml ether. The organic layers were combined, extracted 2×20 ml 1N NaOH and then 2×20 ml H2O, dried (MgSO4), stripped, and the solid residue recrystallized from ethyl acetate and cyclohexane to yield title product 4.4 g.

Provenance & Evidence