Reaktion #1973960

Reaktionsgleichung

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

potassium carbonate

dimethyl sulfate

→

title compound

Ausbeute 87.0%

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

Ausbeute 87.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle