Reaction #531801

Reaction equation

compound 82

γ-oxo-4-(coronen-1-yl)butanoic acid

hydrazine

sodium hydroxide

→

brownish-red solid

Yield 88.5%

4-(coronen-1-yl)butanoic acid

Yield 88.5%

Solvents

diethylene glycol

Conditions

Workup

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

Procedure

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.

Source