Reacción #9015

Ecuación de reacción

dimethyl sulfate

2-Hydroxy-4-methylbenzonitrile

lithium hydroxide monohydrate

→

2-methoxy-4-methylbenzonitrile

Rendimiento 90.0%

Disolventes

diethyl ether

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 2 hours
2. 2
   Lavadowashed with saturated aqueous NaHCO3 (3×15 mL)
3. 3
   Secadodried (MgSO4)
4. 4
   Concentraciónconcentrated
5. 5
   OtroPurification of the crude material by column chromatography on silica gel (4:1 hexanes-EtOAc)

Procedimiento

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).

Fuente