Reacción #1767

Ecuación de reacción

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente