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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence