Dimethylformamide → HCID 12397048, compound

Participants

Reaction Steps

3 g of 3,4-dihydroxybenzaldehyde and 0.87 g of 60% oily sodium hydride were suspended in 13 ml of tetrahydrofuran, and a dimethylformamide solution (10 ml) of 3.3 ml of methoxymethyl chloride was added. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was distributed between ethyl acetate and water, the organic layer was worked up in a customary manner, and then purified by silica gel column chromatography [Wakogel C-200, 150 g; eluting solvent: hexane/ethyl acetate=4/1] to give 1.78 g (yield 45%) of 3-hydroxy-4-methoxymethyloxybenzaldehyde.

Provenance & Evidence