反应 #1767

反应方程式

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

溶剂

DMF

反应条件

后处理

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice
2. 2
   萃取the resulting aqueous solution extracted with Et2O (3×200 mL)
3. 3
   干燥The organic phase was dried (MgSO4)
4. 4
   过滤filtered
5. 5
   其他the Et2O removed under reduced pressure
6. 6
   其他The crude white solid was purified by pressurized silica gel column chromatography
7. 7
   其他Evaporation of the hexanes

实验过程

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.

来源