Sulfuric Acid → m3OMG

Participants

Reaction Steps

Methyl 3,4,5-trihydroxybenzoate(50.0 g, 270 mmol) prepared in Step 1 and borax(54.0 g, 140 mmol) were dissoved in distilled water(1) and the mixture was stirred for 1 hour. To this solution was added sodium hydroxide(13 g, 330 mmol) dissoved in distilled water(100 ml), and the resulting mixture was stirred for 10 minutes. Dimethylsulfate(135 ml, 370 mmol) was added and the mixture was stirred again for 15 hours. The reaction solution was neutralized to pH 7-8 using conc. sulfuric acid, extracted with ethyl acetate and then subjected to silica gel column chromatography(eluent: ethyl acetate/n-hexane, 1/2, v/v) to give methyl 3,4-dihydroxy-5-methoxybenzoate(42.5 g, Yield 79%) as a white solid.

Provenance & Evidence