Acetone → HCID 71278892, compound

Participants

Reaction Steps

2,5-Dihydroxy-3-methylbenzoic acid (4.7 g, 29 mmol) was added successively with acetone (40 mL), dimethyl sulfate (9.0 g, 71 mmol), and potassium carbonate (10 g, 72 mmol), and the mixture was stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure, the residue was added with ethyl acetate, and then the organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with acetone (50 mL), potassium carbonate (1.0 g, 72 mmol), and methyl bromoacetate (6.6 g, 43 mmol), and then the mixture was refluxed for 8 hours by heating. The reaction mixture was filtered through Celite, and then the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, and the organic layer was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with hexane/ethyl acetate (70:30→50:50)) to obtain methyl 5-methoxy-2-(2-methoxy-2-oxoethoxy)-3-methylbenzoate (4.9 g, 63%).

Provenance & Evidence