反应 #9015

反应方程式

dimethyl sulfate

2-Hydroxy-4-methylbenzonitrile

lithium hydroxide monohydrate

→

2-methoxy-4-methylbenzonitrile

收率 90.0%

溶剂

diethyl ether

THF

反应条件

后处理

1. 1
   温度to reflux for 2 hours
2. 2
   洗涤washed with saturated aqueous NaHCO3 (3×15 mL)
3. 3
   干燥dried (MgSO4)
4. 4
   浓缩concentrated
5. 5
   其他Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

实验过程

To a solution of 2-Hydroxy-4-methylbenzonitrile (0.46 g, 3.46 mmol) in THF (17 mL) was added lithium hydroxide monohydrate (0.292 g, 6.95 mmol) followed by dimethyl sulfate (0.50 mL, 5.28 mmol). The resultant mixture was heated to reflux for 2 hours then cooled to room temperature. The mixture was diluted with diethyl ether (50 mL), washed with saturated aqueous NaHCO3 (3×15 mL), dried (MgSO4) and concentrated. Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc) provided 0.456 g (90%) of 2-methoxy-4-methylbenzonitrile as a white solid. 1H NMR (CDCl3) δ 2.41 (s, 3H), 3.91 (s, 3H), 6.77 (s, 1H), 6.81 (d, 1H, J=6Hz), 7.43 (d, 1H, J=6 Hz). ES-MS m/z 148 (M+H).

来源