Reaction #531798

Reaction equation

perylene

succinic anhydride

aluminum chloride

→

brownish solid

Yield 100.2%

γ-oxo-4-(perylen-1-yl)butanoic acid

Yield 100.2%

Solvents

methylene chloride

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.ADDITION40 ml of cooled 2M hydrochloric acid was added
5. 5
   workup.WAITfollowed by 30-minute
6. 6
   workup.STIRRINGstirring
7. 7
   OtherThe solid substance obtained here
8. 8
   Filtrationwas collected by filtration
9. 9
   workup.ADDITIONThis solid substance was dispersed in 100 ml of xylene
10. 10
    Temperaturewas heated to 140° C.
11. 11
    Extractionto extract the impurities
12. 12
    TemperatureAfter the substance was cooled slowly back to room temperature
13. 13
    Filtrationthe solid substance was collected by filtration
14. 14
    Otherwas dried under reduced pressure

Procedure

The perylene 71 (5.01 g, 19.8 mmol) and 4.34 g (43.4 mmol) of succinic anhydride were put into a 500-ml three-inlet flask, and a nitrogen substitution was performed. The substance obtained here was immersed in an ice bath. After 16.3 g (122 mmol) of aluminum chloride dispersed in 200 ml of methylene chloride was slowly dripped onto the substance, the reaction container was removed from the ice bath, and the substance was stirred at room temperature for 13 hours. After the reaction was completed, 40 ml of cooled 2M hydrochloric acid was added, followed by 30-minute stirring. The solid substance obtained here was collected by filtration. This solid substance was dispersed in 100 ml of xylene, and was heated to 140° C., to extract the impurities. After the substance was cooled slowly back to room temperature, the solid substance was collected by filtration, and was dried under reduced pressure, to obtain 6.99 g of the brownish solid substance 72.

Source