تفاعل #9015

معادلة التفاعل

dimethyl sulfate

2-Hydroxy-4-methylbenzonitrile

lithium hydroxide monohydrate

→

2-methoxy-4-methylbenzonitrile

المردود 90.0%

المذيبات

diethyl ether

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto reflux for 2 hours
2. 2
   غسيلwashed with saturated aqueous NaHCO3 (3×15 mL)
3. 3
   تجفيفdried (MgSO4)
4. 4
   تركيزconcentrated
5. 5
   أخرىPurification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

الإجراء التجريبي

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).

المصدر