Dimethylformamide → 2-(benzyloxy)-1-naphthaldehyde

Participants

Reaction Conditions

Reaction Steps

450 ml of a dimethylformamide solution containing 100 g (0.58 mole) of 2-hydroxy-1-naphthaldehyde and 96.3 g (0.7 mole) of anhydrous potassium carbonate was stirred with heating at 60° C. To the solution was added dropwise 88.3 g (0.7 mole) of benzyl chloride. After the completion of the dropwise addition, the mixture was stirred at 60° C. for 2 hours. Then 870 ml of ethyl acetate heated at 60° C. and 1.2 liters of warm water at 60° C. were added to the mixture and it was extracted at 60° C. and separated. The organic layer was concentrated under reduced pressure to about 550 ml. 440 ml of methanol was added to the concentrate, and the solution was cooled to 5° C. to crystallize. The precipitated crystals were collected by filtration, and washed with methanol to obtain 131 g (0.5 mole) of 2-benzyloxy-1-naphthaldehyde.

Provenance & Evidence