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- Experimental procedure: To a mixture of 3-nitrobenzaldehyde (500 mg, 3.31 mmole) and nitroethane (272 mg, 3.63 mmole) in water (5 ml) and THF (0.4 ml) was added 1 drop of benzyltrimethylammonium hydroxide (40% aq. solution) at room temperature. The mixture was stirred at room temperature for 4 min. After the reaction was complete (TLC), excess water was added and the aqueous layer was extracted with chloroform (2 × 20 ml). The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography to afford 1-(3-nitrophenyl)-2-nitropropan-1-ol (734 mg, 98%); 1H NMR (200 MHz, CDCl3): δ 1.40 (d, J = 7.3 Hz, 3H), 3.46 (d, J = 4 Hz, 1H, D2O exchangeable), 4.70–4.85 (m, 1H), 5.22 (dd, J = 7.5 Hz, 4 Hz, 1H), 7.60 (t, J = 8.1 Hz, 1H), 7.70–7.80 (m, 1H), 8.15–8.30 (m, 2H); MS (m/z rel. intensity %) 226 M+ (5), 179 (45), 151 (76), 150 (95), 149 (100), 135 (8), 121 (5), 115 (10), 105 (50), 90 (9) and 77 (52)