1-Nitropropane → HCID 2826291, compound

Participants

Reaction Conditions

Reaction Steps

3-Benzyloxy-4-methoxybenzaldehyde (24.23 g, 100 mmol) and ammonium acetate (7.73 g, 100 mmol) were covered with 1-nitropropane (90 mL, 1008 mmol) and heated to 160° C. for 22 h. The reaction mixture was then cooled to room temperature and the excess of 1-nitropropane was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL), washed with water (100 mL), brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was boiled up in ethanol (100 mL). After cooling to room temperature the yellow precipitate was collected on a sinter funnel and washed with ethanol (4×30 mL). The solid was dried in vacuo to give the title compound as yellow powder (14.07 g, 44%). 1H NMR (270 MHz, CDCl3) δ 1.14 (3H, t, J 7.3, CH2CH3), 2.71 (2H, q, J 7.4, CH2CH3), 3.93 (3H, s, OCH3), 5.19 (2H, s, OCH2Ph), 6.91 (1H, d, J 1.9, CH), 6.94 (1H, d, J 8.5, CH), 7.05 (1H, dd, J 8.4, CH), 7.25-7.48 (5H, m, OCH2C6H5), 7.91 (1H, s, HC═CNO2).

Provenance & Evidence