Sodium Thiosulfate → 2-Amino-4-ethylphenol

反応式

[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([N+:10]([O-])=O)[CH:4]=1)[CH3:2].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)C.O>[NH2:10][C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[CH:8]=[CH:7][C:6]=1[OH:9]

参加物

反応条件

温度: 80 °C

実験手順

To a mixture of 4-ethyl-2-nitrophenol (5.5 g, 0.032 mol) in ethanol (180 mL) and water (90 mL) was added sodium thiosulfate (23 g, 0.131 mol) at room temperature. The heterogeneous mixture was stirred at 80° C. under an atmosphere of nitrogen for 16 hour. The reaction mixture was cooled to room temperature, and ethanol was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3×100 mL), and the organic layer was washed with brine and dried under sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica using 0%-25% methanol/dichloromethane as a mobile phase (×2). The solvent was removed under reduced pressure to give 2-amino-4-ethylphenol (0.89 g, 0.006 mol). 1H NMR (DMSO-d6, 400 MHz) δ 8.61 (br, 2H), 6.47 (d, 1H), 6.37 (s, 1H), 6.18 (d, 1H), 2.17 (q, 2H), 1.08 (t, 3H). MS: MH−: 137