4-Hydroxybenzyl Alcohol → (4-(Propan-2-yloxy)phenyl)methanol

Participants

Reaction Steps

4-Hydroxybenzylalcohol (1 g) in DMF (10 ml) under nitrogen at 0° C. was treated portionwise with sodium hydride (355 mg). The resulting solution was stirred for 0.5 h before isopropyl bromide (0.99 g) was added, and the solution was stirred for a further 18 h. Phosphate buffer (pH=6.5) was then added and the solution was extracted with EtOAc. The combined organic layers were then washed with water, dried (MgSO4) and concentrated in vacuo. The residue was purified by chromatography (Biotage, 90 g) eluting with 40-60° C. petroleum ether-EtOAc (4:1) to give the title compound (931 mg). LCMS RT=2.51 min.

Provenance & Evidence