Реакция #46731

Уравнение реакции

BBr3

2-methoxy-4-nonyl benzoic acid

EtOH H2O

→

product

Выход 23.0%

4-Nonyl salicylic acid

Выход 23.0%

Растворители

HCl

Условия реакции

Обработка

1. 1
   ЭкстракцияThe reaction mixture was extracted with EtOAc (3×)
2. 2
   Сушкаdried (MgSO4)
3. 3
   Фильтрацияfiltered
4. 4
   Другоеevaporated to dryness
5. 5
   workup.DISSOLUTIONThe crude ester was dissolved in CH2Cl2 (10 mL)
6. 6
   Температураto warm to room temperature overnight
7. 7
   workup.ADDITIONpoured onto H2O
8. 8
   Экстракцияextraction with EtOAc
9. 9
   Сушкаdrying (MgSO4)
10. 10
    Фильтрацияfiltering
11. 11
    Другоеevaporation to dryness and column chromatography (SiO2)

Методика

A solution of 2-methoxy-4-nonyl benzoic acid (600 mg; 2.15 mmol) was refluxed overnight in 6 M HCl [50% (w/w) EtOH/H2O; 35 mL). The reaction mixture was extracted with EtOAc (3×) dried (MgSO4), filtered and evaporated to dryness. The crude ester was dissolved in CH2Cl2 (10 mL), cooled to −10° C. and then added 1 M BBr3 (CH2Cl2; 10 mL; 10 mmol). The reaction mixture was allowed to warm to room temperature overnight and then poured onto H2O. Succeeding extraction with EtOAc, drying (MgSO4), filtering, evaporation to dryness and column chromatography (SiO2) yielded 130 mg (23%) product. Mp. 94-97° C.

Источник