Reacción #83992

Ecuación de reacción

Phosphorus oxychloride

N-methylformanilide

2-Methyl resorcinol

→

product

Rendimiento 57.0%

2,4-Dihydroxy-3-methylbenzaldehyde

Rendimiento 57.0%

Disolventes

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in ice
2. 2
   Temperaturato warm to room temperature
3. 3
   workup.STIRRINGwhile stirring overnight
4. 4
   FiltraciónThe precipitated intermediate product was collected by filtration
5. 5
   Lavadorinsed with ether (3×)
6. 6
   workup.DISSOLUTIONby dissolving in a mixture of acetone (250 mL) and water (250 mL)
7. 7
   workup.STIRRINGstirring for 30 minutes
8. 8
   workup.ADDITIONWater (2 L) was added
9. 9
   Temperaturato cool
10. 10
    OtroThis was recrystallized a second time from water (4 L)

Procedimiento

Phosphorus oxychloride (80 mL, 0.86 mol) was added to a stirred mixture of N-methylformanilide (102 mL, 0.82 mol) in ether (250 mL). The mixture was stirred for 1 hour at room temperature and then cooled in ice. 2-Methyl resorcinol (Aldrich, 100 g, 0.81 mol) was added and the mixture was allowed to warm to room temperature while stirring overnight. The precipitated intermediate product was collected by filtration and rinsed with ether (3×). The intermediate was hydrolyzed by dissolving in a mixture of acetone (250 mL) and water (250 mL) and stirring for 30 minutes. Water (2 L) was added, the mixture was brought to a boil, and then allowed to cool and deposit crystalline product. This was recrystallized a second time from water (4 L) to afford pure product (70 g, 57%). M.p. 150° C. (Lit. 152°-3° C. [W. Baker et al., J. Chem. Soc. 2834-5 (1949)⟧

Fuente