Synthesis
Example 13A Synthesis of 2-hydroxy-1-(4-nitrophenyl)ethanone: 2-bromo-1-(4-nitrophenyl)ethanone (5 g, 20.5 mmol) and silver nitrate (5 g, 29.4 mmol) were dissolved in a solvent mixture of water (250 mL) and acetone (150 mL) and heated to reflux the reaction for 4 hours. After the reaction was completed, it was cooled to room temperature. The reaction mixture was filtered and the filtrate was extracted twice with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. The concentrate was purified by silica gel fast column chromatography with 2:1 hexane/ethyl acetate as eluent to give 3.7 g (50% yield) of the target product 2-hydroxy-1-(4-nitrophenyl)ethanone. Thin layer chromatography (TLC) showed an Rf value of 0.4 (eluent ratio 1:1 hexane/ethyl acetate).
References
[1] Advanced Synthesis and Catalysis, 2016, vol. 358, # 1, p. 74 - 80
[2] Journal of Organic Chemistry, 1989, vol. 54, # 18, p. 4473 - 4474
[3] European Journal of Medicinal Chemistry, 2013, vol. 67, p. 142 - 151
[4] Patent: US2003/225098, 2003, A1. Location in patent: Page 32
[5] Chemische Berichte, 1889, vol. 22, p. 203
