4-Hydroxybenzaldehyde → 2-(Propargyloxy)benzaldehyde

反応式

O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]#C>C1(C)C=CC=CC=1.CC(C)=O>[CH2:10]([O:13][C:8]1[CH:9]=[CH:2][CH:3]=[CH:4][C:5]=1[CH:6]=[O:7])[C:16]#[CH:17]

参加物

実験手順

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).