Succinic anhydride → HCID 54489600, compound

HRID 444618Notes

Reaction equation

HRID 444618 reaction equation
[CH:1]1[C:18]2[C:19]3[C:24]4[C:3](=[CH:4][CH:5]=[C:6]5[C:23]=4[C:22]4[C:9](=[CH:10][CH:11]=[C:12]6[C:21]=4[C:20]=3[C:15](=[CH:16][CH:17]=2)[CH:14]=[CH:13]6)[CH:8]=[CH:7]5)[CH:2]=1.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1.[Cl-].[Al+3].[Cl-].[Cl-]>[N+](C1C=CC=CC=1)([O-])=O>[O:31]=[C:25]([C:2]1[C:3]2[C:24]3[C:19]4[C:18](=[CH:17][CH:16]=[C:15]5[C:20]=4[C:21]4[C:12](=[CH:11][CH:10]=[C:9]6[C:22]=4[C:23]=3[C:6](=[CH:5][CH:4]=2)[CH:7]=[CH:8]6)[CH:13]=[CH:14]5)[CH:1]=1)[CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 9115CoroneneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 54489600HCID 54489600, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

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.

Workup

  1. customThe substance obtained here
  2. customwas immersed in an ice bath
  3. customthe reaction container was removed from the ice bath
  4. addition10 ml of cooled 2M hydrochloric acid was added
  5. waitfollowed by 10-minute
  6. stirringstirring
  7. temperatureThe substance was cooled slowly down to room temperature
  8. customto precipitate a solid substance
  9. filtrationThe solid substance was collected by filtration
  10. additionThis solid substance was dispersed in 20 ml of xylene
  11. temperaturewas heated to 140° C
  12. dissolutionIn this manner, the solid substance was dissolved
  13. temperatureThe substance was then cooled slowly back to room temperature
  14. customto precipitate a solid substance
  15. customThe solid substance obtained here
  16. filtrationwas collected by filtration
  17. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-7c7cba9854de450c9183c3c10eb85596
Source dataset
uspto-grants-2013_07
Patent number
US08475685B2

Reaction notes

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