Benzyl Bromide → 2-benzyloxy-3-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 2-hydroxy-3-methylbenzaldehyde 20.0 g (147 mmol) prepared by the above 1-(1) in dimethylformamide (DMF) (100 ml) was added to the suspension of sodium hydride 6.5 g (163 mmol) with purity 60% and DMF (40 ml) under ice-cooling. After completion of emission of hydrogen gas, benzyl bromide 25.0 g (147 mmol) was dropped to it in a ice bath. The reaction mixture was stirred for 4 hours at 20° C. After the disappearance of the raw material, water was added to the reaction mixture and it was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed in vacuo and the residue was purified by silica gel chromatography (n-hexane-ethyl acetate) to give 2-benzyloxy-3-methylbenzaldehyde 29.9 g (yield: 91%).

Provenance & Evidence