4-Methyl-3-nitrophenol

119-32-4

2042-14-0

General procedure for the synthesis of 4-methyl-3-nitrophenol from 4-methyl-3-nitroaniline: 4-methyl-3-nitroaniline (200 mg, 1.31 mmol) was dissolved in a 3:1 mixture of H2SO4-H2O. The resulting mixture was heated to 100 °C and kept for 30 min. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and NaNO2 solution was added slowly and dropwise. After the dropwise addition was completed, the reaction was continued for 1 hour, after which the mixture was heated to reflux. After the reaction was complete, the reaction mixture was extracted several times with EtOAc, the organic phases were combined and dried with anhydrous Na2SO4, and subsequently concentrated. The crude product was purified by fast column chromatography (eluent ratio: petroleum ether-ethyl acetate 9:1) to give a yellow solid in 70% yield. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.48 (s, 1H), 7.17 (d, J = 8.4 Hz, 1H), 7.01 (dd, J = 8.4, 2.4 Hz, 1H), 5.84 (s, 1H), 2.48 (s, 3H) ppm.