Реакция #531801

Уравнение реакции

compound 82

γ-oxo-4-(coronen-1-yl)butanoic acid

hydrazine

sodium hydroxide

→

brownish-red solid

Выход 88.5%

4-(coronen-1-yl)butanoic acid

Выход 88.5%

Растворители

diethylene glycol

Условия реакции

Обработка

1. 1
   workup.WAITfollowed by 90-minute
2. 2
   Температураrefluxing in a 180-° C
3. 3
   workup.DISTILLATIONThe excess hydrazine and water were distilled away
4. 4
   Другоеto precipitate a solid substance
5. 5
   ФильтрацияThe solid substance was collected by filtration
6. 6
   Промывкаwas washed with ion-exchange water
7. 7
   Другоеby drying under reduced pressure
8. 8
   workup.ADDITIONThis solid substance was dispersed in 10 ml of xylene
9. 9
   Температураwas heated to 140° C
10. 10
    workup.DISSOLUTIONIn this manner, the solid substance was dissolved
11. 11
    ТемператураAfter that, the substance was cooled slowly back to room temperature
12. 12
    Другоеto precipitate a solid substance
13. 13
    ФильтрацияThe solid substance generated here was collected by filtration
14. 14
    Другоеwas dried under reduced pressure

Методика

The compound 82 (0.503 g, 1.26 mmol), 0.4 ml of 79% aqueous hydrazine, and 0.462 g (11.6 mmol) of sodium hydroxide were dissolved in 3.0 ml of diethylene glycol, followed by 90-minute refluxing in a 180-° C. oil bath. The excess hydrazine and water were distilled away, and the refluxing was continued for two more hours. After the reaction was completed, the solution was cooled back to room temperature, to precipitate a solid substance. The solid substance was collected by filtration, and was washed with ion-exchange water, followed by drying under reduced pressure. This solid substance was dispersed in 10 ml of xylene, and was heated to 140° C. In this manner, the solid substance was dissolved. After that, the substance was cooled slowly back to room temperature, to precipitate a solid substance. The solid substance generated here was collected by filtration, and was dried under reduced pressure, to obtain 0.431 g of the brownish-red solid substance 83. Here, 1HNMR was not measured, since its product was not soluble in any deuterated solvents.

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