Catechol → Nitrocatechol

Participants

Reaction Steps

To a solution of pyrocatechol (60 g, 0.54 mol) in ether (2000 mL) at 0° C. was added fuming nitric acid (24 mL) dropwise. After the addition was over, the reaction was allowed to stand at room temperature for 20 minutes, decanted into ice-water and the resulting solution was extracted with ether. The combined organic extracts were neutralized with aqueous sodium carbonate (10%), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue obtained was purified by silica gel column chromatography (petroleum ether/ethyl acetate 5/1) to afford the product 3-nitrobenzene-1,2-diol (25 g, yield 30%). 1H NMR (400 MHz, CDCl3) δ ppm 10.62 (s, 1H), 7.64-7.67 (dd, 1H, J=1.6 Hz, 8.8 Hz), 7.23-7.26 (m, 1H), 6.89-6.93 (t, 1H, J=8.4 Hz), 5.79 (br, 1H).

Provenance & Evidence