Reaction #531800

Reaction equation

coronene

succinic anhydride

aluminum chloride

→

yellow-green solid

Yield 88.4%

γ-oxo-4-(coronen-1-yl)butanoic acid

Yield 88.4%

Solvents

nitrobenzene

Conditions

Workup

1. 1
   OtherThe substance obtained here
2. 2
   Otherwas immersed in an ice bath
3. 3
   Otherthe reaction container was removed from the ice bath
4. 4
   workup.ADDITION10 ml of cooled 2M hydrochloric acid was added
5. 5
   workup.WAITfollowed by 10-minute
6. 6
   workup.STIRRINGstirring
7. 7
   TemperatureThe substance was cooled slowly down to room temperature
8. 8
   Otherto precipitate a solid substance
9. 9
   FiltrationThe solid substance was collected by filtration
10. 10
    workup.ADDITIONThis solid substance was dispersed in 20 ml of xylene
11. 11
    Temperaturewas heated to 140° C
12. 12
    workup.DISSOLUTIONIn this manner, the solid substance was dissolved
13. 13
    TemperatureThe substance was then cooled slowly back to room temperature
14. 14
    Otherto precipitate a solid substance
15. 15
    OtherThe solid substance obtained here
16. 16
    Filtrationwas collected by filtration
17. 17
    Otherwas dried under reduced pressure

Procedure

The coronene 81 (0.699 g, 2.33 mmol) and 0.514 g (5.14 mmol) of succinic anhydride were put into a 100-ml two-inlet flask, and a nitrogen substitution was performed. The substance obtained here was immersed in an ice bath. After 2.80 g (21.0 mmol) of aluminum chloride dispersed in 20 ml of nitrobenzene was slowly dripped onto the substance, the reaction container was removed from the ice bath, and the substance was stirred at room temperature for 5 hours. After the reaction was completed, 10 ml of cooled 2M hydrochloric acid was added, followed by 10-minute stirring. The substance was cooled slowly down to room temperature, to precipitate a solid substance. The solid substance was collected by filtration. This solid substance was dispersed in 20 ml of xylene, and was heated to 140° C. In this manner, the solid substance was dissolved. The substance was then cooled slowly back to room temperature, to precipitate a solid substance. The solid substance obtained here was collected by filtration, and was dried under reduced pressure, to obtain 0.825 g of the yellow-green solid substance 82.

Source