반응 #9015

반응 방정식

dimethyl sulfate

2-Hydroxy-4-methylbenzonitrile

lithium hydroxide monohydrate

→

2-methoxy-4-methylbenzonitrile

수율 90.0%

용매

diethyl ether

THF

반응 조건

후처리

1. 1
   온도to reflux for 2 hours
2. 2
   세척washed with saturated aqueous NaHCO3 (3×15 mL)
3. 3
   건조dried (MgSO4)
4. 4
   농축concentrated
5. 5
   기타Purification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

실험 절차

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).

출처