4-Nitrophenol → 2'-Hydroxy-5'-nitroacetophenone

Temperature

50 °C

4-Nitrophenol (1.61 g, 11.6 mmol) was dissolved in dichloroethane (10 ml) and aluminum chloride (2.31 g, 17.3 mmol) was slowly added in three portions. The addition of acetylchloride (0.818 ml, 11.51 mmol) was followed by stirring at 50° C. for 2 hours. The reaction was terminated with the addition of ice water (10 ml) and 2N hydrochloric acid solution (10 ml) at 0° C. The reaction mixture was extracted with dichloroethane (10 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated using vacuum evaporation. The crude product was purified by chromatography on silica gel to give the title compound (Yield 78%).

1. customThe reaction was terminated with the addition of ice water (10 ml) and 2N hydrochloric acid solution (10 ml) at 0° C
2. extractionThe reaction mixture was extracted with dichloroethane (10 ml)
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. concentrationconcentrated
5. customvacuum evaporation
6. customThe crude product was purified by chromatography on silica gel

ORD record

ord-6822fffef08c4a37ae1e80fb22750161

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812045B2