Reacción #2546

Ecuación de reacción

4-Chloromethyl-N-(2-methoxyphenyl)benzamide

calcium carbonate

dioxane water

→

title compound

Rendimiento 88.3%

4-Hydroxymethyl-N-(2-methoxyphenyl)benzamide

Rendimiento 88.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaof heating
2. 2
   Temperaturaunder reflux
3. 3
   Filtraciónfiltering off the formed insoluble materials
4. 4
   Otrothe organic solvent was removed by evaporation
5. 5
   ExtracciónThe thus obtained residue was extracted with ethyl acetate
6. 6
   Lavadothe resulting organic layer was washed with saturated brine
7. 7
   Secadodried on anhydrous magnesium sulfate
8. 8
   OtroAfter removing the solvent
9. 9
   Otroby evaporation
10. 10
    Otrothe resulting colorless solid material was purified

Procedimiento

4-Chloromethyl-N-(2-methoxyphenyl)benzamide (500 mg, 1.81 mmol) and precipitated calcium carbonate (970 mg, 9.7 mmol) were suspended in a dioxane-water (1:1) mixture solution (9 ml) and subjected to 25 hours of heating under reflux. After adding THF (25 ml) and filtering off the formed insoluble materials, the organic solvent was removed by evaporation. The thus obtained residue was extracted with ethyl acetate, and the resulting organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation, the resulting colorless solid material was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:1), thereby obtaining 411 mg (88.3%) of the title compound in the form of colorless crystals.

Fuente