Methyl iodide → 3-Hydroxy-2-methoxybenzaldehyde

Participants

Reaction Steps

To a solution of 2,3-dihydroxybenzaldehyde (20.0 g) in dimethylsulfoxide (80 ml) was added sodium hydride (5.79 g), and the mixture was stirred at room temperature for 1 hr. Methyl iodide (9.0 ml) was added, and the mixture was further stirred at room temperature for 20 hrs. The obtained reaction mixture was partitioned between ethyl acetate (1000 ml) and water (500 ml). The aqueous layer was further extracted with ethyl acetate (1000 ml). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography and crystallized from diisopropyl ether and hexane to give 3-hydroxy-2-methoxybenzaldehyde (11.5 g) as pale-brown crystals.

Provenance & Evidence