Реакция #214194

Уравнение реакции

sodium hydroxide

ethyl 2-(p-formylphenyl)propionate

cycloheptanone

→

desired product

Выход 39.7%

2-[4-(2-Oxo-1-cycloheptylidenemethyl)phenyl]propionic acid

Выход 39.7%

Растворители

Условия реакции

Обработка

1. 1
   Температураthe resulting mixture was heated
2. 2
   Температураunder reflux for 3 hours
3. 3
   ТемператураAfter cooling
4. 4
   Экстракцияthe reaction mixture was extracted twice with ethyl acetate
5. 5
   Экстракцияextracted with ethyl acetate
6. 6
   ПромывкаThe extract was washed with water
7. 7
   Сушкаdried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONThe ethyl acetate was distilled off
9. 9
   Другоеto leave an oily substance, which
10. 10
    Промывкаwas then subjected to a silica gel column chromatography and elution
11. 11
    Другоеto yield an yellow oily substance
12. 12
    workup.DISTILLATIONThe substance was distilled under reduced pressure

Методика

To a mixture of 5.15 g of ethyl 2-(p-formylphenyl)propionate and 4.2 g of cycloheptanone were added dropwise at room temperature 30 ml of an aqueous solution of 2.6 g of sodium hydroxide and the resulting mixture was heated under reflux for 3 hours. After cooling, the reaction mixture was extracted twice with ethyl acetate, an aqueous layer was made acidic with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The ethyl acetate was distilled off to leave an oily substance, which was then subjected to a silica gel column chromatography and elution was effected with benzene-ethyl acetate 5:1 to yield an yellow oily substance. The substance was distilled under reduced pressure to give 2.7 g of the desired product as a pale yellow oily substance having a boiling point of 210°-215° C./0.3 mmHg (bath temp.).

Источник