Reacción #309518

Ecuación de reacción

4-hydroxy-3-methylbenzaldehyde

hydroxyl ammonium chloride

→

title compound

Rendimiento 66.0%

4-Hydroxy-3-methylbenzonitrile

Rendimiento 66.0%

Disolventes

diethyl ether

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 90 minutes
3. 3
   OtroThe cooled reaction mixture
4. 4
   Lavadowashed with water (30 mL)
5. 5
   LavadoThe combined organic solution was washed with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   Otrothe residue was purified by column chromatography on silica gel
9. 9
   Lavadoeluting with dichloromethane

Procedimiento

A mixture of 4-hydroxy-3-methylbenzaldehyde (530 mg, 3.91 mmol) and hydroxyl ammonium chloride (406 mg, 5.81 mmol) in acetic acid (5 mL) was heated under reflux for 90 minutes. The cooled reaction mixture was then diluted with diethyl ether (30 mL) and washed with water (30 mL). The combined organic solution was washed with brine, dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 97.5:2.5, to afford the title compound as a pale yellow oil in 66% yield, 345 mg.

Fuente