Hydrogen Peroxide (35% in Water)

• p-Anisidine [A0487]
• Hydrogen Peroxide (35% in Water) [H1222]
• Potassium Carbonate [P1748]
• Acetonitrile

To a solution of p-anisidine (123 mg, 1.0 mmol) and potassium carbonate (138 mg, 1.0 mmol) in acetonitrile (5 mL) was added hydrogen peroxide aq. (35%, 0.5 mL) at r.t. and the mixture was stirred at r.t. for 1 h. Potassium carbonate (138 mg, 1.0 mmol) and hydrogen peroxide aq. (0.5 mL) were further added at r.t. and the mixture was stirred at r.t. for overnight. The reaction mixture was diluted with dichloromethane (25 mL) and washed with saturated sodium thiosulfate aq. (50 mL), saturated aqueous sodium bicarbonate solution (50 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, dichloromethane:hexane = 0:1 - 1:4), giving 4-nitroanisole as a pale yellow solid (108 mg, 70% yield).

The reaction mixture was monitored by UPLC.

4-Nitroanisole

¹H NMR (270 MHz, CDCl₃); δ 8.21 (d, 2H, J = 9.2 Hz), 6.96 (d, 2H, J = 9.2 Hz), 3.91 (s, 3H).

• Base promoted peroxide systems for the efficient synthesis of nitroarenes and benzamides
• S. Gupta, A. Ansari, K. V. Sashidhara, Tetrahedron Lett. 2019, 60, 151076.