Acetic Acid → HCID 86681917, compound

Participants

Reaction Conditions

Reaction Steps

The synthesis was performed with reference to the known literature (Bioorganic & Medicinal Chemistry Letters, Vol. 17, p. 6354, 2007). 2-(Carboxymethoxy)-5-methoxy-3-methylbenzoic acid (3.9 g, 16 mmol) was successively added with acetic acid (12 mL), acetic anhydride (20 mL), and sodium acetate (4.0 g), and the mixture was stirred at 120° C. for 4 hours. The reaction mixture was added with ethyl acetate, and the organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the residue was successively added with methanol (40 mL), water (10 mL), and concentrated hydrochloric acid (1.0 mL), and the mixture was refluxed for 1 hour by heating. The solvent was evaporated under reduced pressure, then the residue was dissolved in ethyl acetate, and the solution was washed successively with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the solid formed was suspended in hexane/ethyl acetate (90:10) and thereby washed to obtain 5-methoxy-7-methylbenzofuran-3(2H)-one (0.25 g, 8%).

Provenance & Evidence