3-(4-NITROPHENYL)PROPANOIC ACID

107-94-8

100-02-7

10572-16-4

To a 500 mL three-necked flask was added 4-nitrophenol (15 g, 108 mmol), 3-chloropropionic acid (11.6 g, 108 mmol), an aqueous ethanol solution (150 mL) and a 20% aqueous potassium hydroxide solution (150 mL). The reaction mixture was heated to reflux for 6 hours. After completion of the reaction, the mixture was cooled to room temperature and the pH was adjusted to 1-3 with dilute hydrochloric acid. the reaction mixture was extracted with ethyl acetate (300 mL x 3), the organic phases were combined and washed with saturated aqueous sodium chloride solution (300 mL x 2). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether=1:4, v/v) to afford 3-(4-nitrophenoxy)propionic acid (8.8 g, yield 38.6%) as a white solid.