3-Hydroxybenzyl alcohol → 3-(2-Propyn-1-yloxy)benzenemethanol

Participants

Reaction Steps

To an aqueous solution of 3-hydroxybenzyl alcohol (2.00 g, 16.1 mmol) in sodium hydroxide (35 mL, 1.5 M) was added propargyl bromide (2.11 g, 17.7 mmol), and the mixture was stirred at room temperature for 24 hours. The reaction mixture was extracted with diethyl ether and washed with a 1.5 M aqueous sodium hydroxide solution and saturated brine, and the organic layer was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=5:5) to give the title compound (0.82 g, yield 31%) as an oily matter.

Provenance & Evidence