반응 #1767

반응 방정식

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

용매

DMF

반응 조건

후처리

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

실험 절차

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.

출처