تفاعل #1767

معادلة التفاعل

methyl 4-benzyloxy-2-hydroxybenzoate

NaH

methyl iodide

→

methyl 4-benzyloxy-2-methoxybenzoate

المذيبات

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر