反应详情

A mixture of 1-(2-methoxyethoxy)-4-nitrobenzene (0.724 g, 3.67 mmol) and 10% Pd/C (Aldrich) (0.201 g, 1.89 mmol) in EtOH (10 mL) was evacuated under vacuum and refilled with hydrogen (4 times). The mixture was hydrogenated under balloon pressure at rt for 1.5 h. The reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH) and concentrated. The crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%) to give 4-(2-methoxyethoxy)aniline (0.548 g, 89% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 6.73-6.82 (m, 2H); 6.58-6.68 (m, 2H); 4.01-4.08 (m, 2H); 3.67-3.76 (m, 2H); 3.29-3.52 (m, 5H). m/z (ESI, +ve ion) 168.1 (M+H)+.

1. customwas evacuated under vacuum
2. additionrefilled with hydrogen (4 times)
3. filtrationThe reaction mixture was filtered through a pad of Celite® (diatomaceous earth) (eluent:EtOH)
4. concentrationconcentrated
5. customThe crude product was purified by silica gel chromatography (25 g, eluent: EtOAc in hexanes 0%-60%)