3-Aminophenol → 3-Ethoxymethoxyphenylamine

反応式

[H-].[Na+].[NH2:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[CH2:11]([O:13][CH2:14]Cl)[CH3:12]>C(#N)C>[CH2:11]([O:13][CH2:14][O:10][C:6]1[CH:5]=[C:4]([NH2:3])[CH:9]=[CH:8][CH:7]=1)[CH3:12]

参加物

反応条件

温度: 0 °C

実験手順

A dispersion of 12 g (274.9 mmol) of sodium hydride (55% in oil) was added portionwise at 0° C. to a solution of 20.0 g (183.3 mmol) of 3-aminophenol in 450 mL of dried acetonitrile. The mixture was then allowed to agitate at 0° C. for 3 hours. A solution of 25 g (210.8 mmol) of chloromethyl ethyl ether in 30 mL of acetonitrile was added dropwise, and the mixture was allowed to agitate overnight at room temperature. The reaction mixture was then filtered and the filter cake was washed with a small amount of acetone. The combined filtrates were evaporated. This gave 32.3 g of 3-ethoxymethoxyphenylamine. The resulting crude product was used in the next step without further purification.