反応 #9015

反応方程式

dimethyl sulfate

2-Hydroxy-4-methylbenzonitrile

lithium hydroxide monohydrate

→

2-methoxy-4-methylbenzonitrile

収率 90.0%

溶媒

diethyl ether

THF

反応条件

後処理

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

実験手順

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).

出典