Реакция #1973960

Уравнение реакции

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

potassium carbonate

dimethyl sulfate

→

title compound

Выход 87.0%

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

Выход 87.0%

Растворители

acetone

Условия реакции

Обработка

1. 1
   Температураto reflux for 16 h
2. 2
   ФильтрацияThe mixture was then filtered
3. 3
   Промывкаthe solid was washed with ethyl acetate
4. 4
   КонцентрированиеThe resulting organic liquid was then concentrated under vacuum to an oil
5. 5
   workup.DISSOLUTIONredissolved in ethyl acetate (600 mL)
6. 6
   ПромывкаThe organic solution was then washed with water
7. 7
   Другоеdried
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated under vacuum to an oil that
10. 10
    Другоеwas then subjected to purification via column chromatography (gradient of 5% to 40% EtOAc/Hexanes)

Методика

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%).

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