Reaction #1767

Reaction equation

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

Solvents

DMF

Conditions

Workup

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

Procedure

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.

Source