Reacción #1973960

Ecuación de reacción

Methyl 3-tert-butyl-2-hydroxy-5-nitrobenzoate

potassium carbonate

dimethyl sulfate

→

title compound

Rendimiento 87.0%

methyl 3-tert-butyl-2-methoxy-5-nitrobenzoate

Rendimiento 87.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato reflux for 16 h
2. 2
   FiltraciónThe mixture was then filtered
3. 3
   Lavadothe solid was washed with ethyl acetate
4. 4
   ConcentraciónThe resulting organic liquid was then concentrated under vacuum to an oil
5. 5
   workup.DISSOLUTIONredissolved in ethyl acetate (600 mL)
6. 6
   LavadoThe organic solution was then washed with water
7. 7
   Otrodried
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under vacuum to an oil that
10. 10
    Otrowas then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes)

Procedimiento

Methyl 3-tert-butyl-2-hydroxy-5-nitrobenzoate (11.41 g, 45.0 mmol), potassium carbonate (9.34 g, 67.6 mmol), acetone (200 mL), and dimethyl sulfate (6.46 g, 67.6 mmol) were added together. The resultant mixture was then heated to reflux for 16 h. The mixture was then filtered and the solid was washed with ethyl acetate. The resulting organic liquid was then concentrated under vacuum to an oil and redissolved in ethyl acetate (600 mL). The organic solution was then washed with water, dried, filtered and concentrated under vacuum to an oil that was then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes) to yield the title compound as an oil (10.42, 87%).

Fuente