Benzyl Bromide → Methyl 4-(benzyloxy)-2-hydroxybenzoate

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.

1. filtrationThe reaction solution was filtered through celite
2. dissolutionThe crude oil was dissolved in EtOAc (1000 mL)
3. washwashed with water (250 mL), and saturated aqueous NaHCO3 (500 mL)
4. dry with materialThe EtOAc layer was dried (MgSO4)
5. filtrationfiltered
6. customthe EtOAc was removed under reduced pressure
7. customThe crude product was purified by pressurized silica gel column chromatography
8. customEvaporation of the hexanes

ORDレコード

ord-b4fd402e735143d2ba1df2c8a9a0fe8f

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05726172