Реакция #1767

Уравнение реакции

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice
2. 2
   Экстракцияthe resulting aqueous solution extracted with Et2O (3×200 mL)
3. 3
   СушкаThe organic phase was dried (MgSO4)
4. 4
   Фильтрацияfiltered
5. 5
   Другоеthe Et2O removed under reduced pressure
6. 6
   ДругоеThe crude white solid was purified by pressurized silica gel column chromatography
7. 7
   ДругоеEvaporation of the hexanes

Методика

To a stirred, 0° C. solution of methyl 4-benzyloxy-2-hydroxybenzoate (12 g, 46 mmol) in DMF (150 mL) was added NaH (2.76 g, 69 mmol) and methyl iodide (7.2 mL, 116 mmol). The solution was allowed to warm to ambient temperature overnight with stirring. The reaction mixture was poured onto ice and the resulting aqueous solution extracted with Et2O (3×200 mL). The organic phase was dried (MgSO4), filtered and the Et2O removed under reduced pressure. The crude white solid was purified by pressurized silica gel column chromatography using 4:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-methoxybenzoate as a white powder.

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