Potassium Carbonate → 2-(2-Acetyl-4-fluorophenoxy)acetic acid

Beteiligte Stoffe

Reaktionsschritte

A solution of 5′-fluoro-2′-hydroxyacetophenone (25.0 g), methyl bromoacetate (27.2 g), potassium carbonate (33.6 g) in N,N-dimethylformamide (250 mL) was stirred at room temperature for 1.5 hr. 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 oil. Tetrahydrofuran (300 mL), ethanol (300 mL) and 1N aqueous sodium hydroxide solution (300 mL) were added to the obtained oil, and the mixture was stirred at room temperature for 30 min. The solvent was concentrated under reduced pressure, 1N hydrochloric acid (300 mL) was added, and the resulting crystals were collected by filtration. The crystals were dissolved in ethyl acetate, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (23.7 g, 69%) as a white solid.

Herkunft & Nachweise