Reaction #1973960

Reaction equation

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

potassium carbonate

dimethyl sulfate

→

title compound

Yield 87.0%

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

Yield 87.0%

Solvents

acetone

Conditions

Workup

1. 1
   Temperatureto reflux for 16 h
2. 2
   FiltrationThe mixture was then filtered
3. 3
   Washthe solid was washed with ethyl acetate
4. 4
   ConcentrationThe resulting organic liquid was then concentrated under vacuum to an oil
5. 5
   workup.DISSOLUTIONredissolved in ethyl acetate (600 mL)
6. 6
   WashThe organic solution was then washed with water
7. 7
   Otherdried
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated under vacuum to an oil that
10. 10
    Otherwas then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes)

Procedure

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%).

Source