3-Hydroxybenzyl alcohol → 2-[3-(Hydroxymethyl)phenoxy]acetonitrile

Participants

Reaction Steps

25.3 g (203.8 mmol) of 3-hydroxybenzyl alcohol are dissolved in 50 ml of dimethylformamide, and 400 ml of acetone and 28.17 g (203.8 mmol) of finely ground potassium carbonate are added. After 5 minutes of stirring, 24.45 g (203.8 mmol) of bromoacetonitrile are added, and the mixture is boiled under reflux for 72 hours. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate and washed with 10% strength aqueous sodium hydroxide solution and then with water. The organic phase is dried over magnesium sulfate and filtered through a short silica gel column (mobile phase toluene->toluene/ethyl acetate=1:1). Evaporation gives 163.18 g (86% of theory) of an oil. Rf (SiO2, toluene/ethyl acetate=1:1)=0.41.

Provenance & Evidence