4-Hydroxybenzaldehyde → 2-(2-Propynyloxy)benzenecarbaldehyde

Participants

Reaction Steps

A solution of 4-hydroxybenzaldehyde (1 g, 8.2 mmol), of potassium carbonate (2.27 g, 16.4 mmol) and of propargyl bromide (1.4 ml of a solution at 80% in toluene) in 50 ml of anhydrous acetone is heated under reflux for 5 hours. The reaction medium is cooled to room temperature, filtered and concentrated. The crude reaction product obtained is purified using a chromatography column on silica gel, eluting with dichloromethane. 1.31 g (quantitative yield) of prop-2-ynyloxybenzaldehyde are obtained in the form of a white solid which is used as it is in the next step. 1H NMR (DMSO-d6, 400 MHZ, δ ppm): 9.89 (s, 1H); 7.89 (d, 2H); 7.18 (d, 2H); 4.95 (s, 2H); 3.65 (s, 1H).

Provenance & Evidence