Реакция #1833636

Уравнение реакции

K2CO3

methyl 2,5-dihydroxybenzoate

bromomethylbenzene

→

methyl 5-(benzyloxy)-2-hydroxybenzoate

Выход 69.0%

Растворители

methanol

CHCl3

methanol CHCl3

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas then added
2. 2
   Температураat reflux for another 4 hours
3. 3
   ТемператураAfter cooling down
4. 4
   Фильтрацияfiltration
5. 5
   Промывкаthe filter cake was washed with CHCl3 (20 mL)
6. 6
   КонцентрированиеThe combined filtrate was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONThe residue was redissolved in CHCl3 (200 mL)
8. 8
   Промывкаwashed with HCl (1N) (100 mL×2)
9. 9
   ПромывкаThe organic was then washed with brine (100 mL)
10. 10
    Сушкаdried over Na2SO4
11. 11
    Фильтрацияfiltered
12. 12
    Концентрированиеconcentrated
13. 13
    ДругоеThe residue was purified by silica gel column chromatography
14. 14
    Промывкаeluting with petroleum ether/EtOAc (8:1)

Методика

To a refluxed suspension of K2CO3 (32.8 g, 238 mmol) in methanol (180 mL) and CHCl3 (350 mL) was then added a mixture of methyl 2,5-dihydroxybenzoate (10.0 g, 59.5 mmol) and bromomethylbenzene (7.10 mL, 59.5 mmol) in methanol/CHCl3 (50 mL/25 mL) drop wise over 30 minutes. The resulting mixture was stirred at reflux for another 4 hours. After cooling down and filtration, the filter cake was washed with CHCl3 (20 mL). The combined filtrate was concentrated under reduced pressure. The residue was redissolved in CHCl3 (200 mL), washed with HCl (1N) (100 mL×2). The organic was then washed with brine (100 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/EtOAc (8:1) to give methyl 5-(benzyloxy)-2-hydroxybenzoate (10.6 g, 69.0%) as a white solid.

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