反应详情

温度

10 °C

To a mixture of methyl 3,5-dihydroxybenzoate (20 g) in N,N-dimethylformamide (200 ml) was added sodium hydride (60% in mineral oil, 5.23 g) slowly at 10° C. After stirring at 10° C. for 30 minutes, benzyl bromoacetate (20.7 ml) was added dropwise to the mixture over 10 minutes. The reaction mixture was stirred at room temperature overnight and then evaporated in vacuo. Ethyl acetate (400 ml) and water (100 ml) was added to the residue and the mixture was adjusted to pH 5 with hydrochloric acid. Two layers were separated and the organic layer was washed successively with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1). The fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-benzyloxycarbonylmethoxy-5-hydroxybenzoate (12.92 g).

1. stirringThe reaction mixture was stirred at room temperature overnight
2. customevaporated in vacuo
3. additionEthyl acetate (400 ml) and water (100 ml) was added to the residue
4. customTwo layers were separated
5. washthe organic layer was washed successively with water and brine
6. dry with materialdried over magnesium sulfate
7. customevaporated in vacuo
8. customThe residue was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (20:1)
9. additionThe fractions containing the desired product
10. customwere collected
11. customevaporated in vacuo