Dimethylformamide → 2-Methoxy-1-naphthaldehyde

Participants

Reaction Conditions

Reaction Steps

500 ml of a dimethylformamide solution containing 103.2 g (0.6 mole) of 2-hydroxy-1-naphthaldehyde and 107.6 g (0.78 mole) of anhydrous potassium carbonate was stirred with heating at 50° C. To the solution was added dropwise 145 g (0.78 mole) of methyl p-toluenesulfonate. After the completion of the dropwise addition, the mixture was stirred at 60° C. for 2 hours. The reaction mixture was added to 1.5 liters of water, and the precipitated crystals were collected by filtration. The crude crystals were recrystallized from a solvent mixture of n-hexane and ethyl acetate (5/1 by volume) to obtain 93.8 g (0.504 mole) of 2-methoxy-1-naphthaldehyde.

Provenance & Evidence