تفاعل #1766

معادلة التفاعل

methyl 2,4-dihydroxybenzoate

K2CO3

benzyl bromide

→

methyl 4-benzyloxy-2-hydroxybenzoate

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction solution was filtered through celite
2. 2
   workup.DISSOLUTIONThe crude oil was dissolved in EtOAc (1000 mL)
3. 3
   غسيلwashed with water (250 mL), and saturated aqueous NaHCO3 (500 mL)
4. 4
   تجفيفThe EtOAc layer was dried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىthe EtOAc was removed under reduced pressure
7. 7
   أخرىThe crude product was purified by pressurized silica gel column chromatography
8. 8
   أخرىEvaporation of the hexanes

الإجراء التجريبي

To a stirred, 0° C. solution of methyl 2,4-dihydroxybenzoate (50 g, 300 mmol) in acetone (1000 mL) was added K2CO3 (150 g, 1000 mmol) and benzyl bromide (330 mmol, 39 mL). The solution was allowed to warm to ambient temperature over 48 h. The reaction solution was filtered through celite and the acetone solution stripped down under reduced pressure. The crude oil was dissolved in EtOAc (1000 mL) and washed with water (250 mL), and saturated aqueous NaHCO3 (500 mL). The EtOAc layer was dried (MgSO4), filtered, and the EtOAc was removed under reduced pressure. The crude product was purified by pressurized silica gel column chromatography using 5:1 hexanes:EtOAc. Evaporation of the hexanes:EtOAc mixture gave the desired methyl 4-benzyloxy-2-hydroxybenzoate as a white powder.

المصدر