Formaldehyde → 3-Hydroxy-5-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of 60% sodium hydride (2.77 g, 69.3 mmol) in N,N-dimethylformamide (50 ml) was gradually added at 0° C. ethanethiol (7 ml), and the solution was stirred at 0° C. for 30 minutes, followed by refluxing under heating for 1 hour. The mixture was cooled to room temperature, and thereto was added 3,5-dimethoxybenzaldehyde (3.84 g, 23.1 mmol) in N,N-dimethylformamide (90 ml) and the mixture was refluxed under heating for 1 hour. The mixture was cooled to room temperature, and thereto were added a saturated aqueous sodium chloride solution (700 ml), 26% aqueous formalin solution (70 ml) and acetic acid (130 ml) in the order. The mixture was stirred, extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution in the order, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified with silica gel chromatography. (hexane:ethyl acetate=2:1) to give the subject compound (2.68 g, 17.6%).

Provenance & Evidence