Nitric Acid → 2-Hydroxy-3-nitrobenzaldehyde

Participants

Reaction Steps

To a solution of 2-hydroxybenzaldehyde (5.0 g, 41 mmol) in acetic acid (50 mL) at 0° C. was added nitric acid (65%, 4 g) dropwise. The reaction mixture was slowly warmed to room temperature for 2 hours and then heated at 40° C. for another 5 hours. The resulting mixture was poured into ice (75 g) and water (500 g). The precipitates were filtrated and purified by silica gel chromatography to afford the product 2-hydroxy-3-nitrobenzaldehyde (1.8 g, yield 26%). 1H NMR (400 MHz, CDCl3) δ ppm 11.44 (s, 1H), 10.42 (s, 1H), 8.34-8.37 (dd, 1H, J=2.0 Hz, 8.4 Hz), 8.10-8.13 (dd, 1H, J=2.0 Hz, 7.6 Hz), 7.12-7.16 (t, 1H, J=8.0 Hz).

Provenance & Evidence