Potassium Carbonate → Acetic acid, 2-(2-acetyl-4-methoxyphenoxy)-

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Reaction Steps

To a mixture of 1-(2-hydroxy-5-methoxyphenyl)ethanone (25.0 g), methyl bromoacetate (15.5 mL) and N,N-dimethylformamide (250 mL) was added potassium carbonate (31.1 g), and the mixture was stirred overnight at room temperature. The insoluble material was filtered off, 1N hydrochloric acid was added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a brown solid. To a mixture of the obtained solid, tetrahydrofuran (300 mL) and ethanol (300 mL) was added 1N aqueous sodium hydroxide solution (300 mL), and the mixture was stirred overnight at room temperature, and concentrated under reduced pressure. 1N Hydrochloric acid (300 mL) was added to the residue at 0° C., and the resulting precipitate was collected by filtration to give the title object compound (34.2 g, quantitative) as a white solid.

Provenance & Evidence