Reacción #531798

ord-e9576a3029d347b9bd67c50ae21200af

Ecuación de reacción

c1cc2cccc3c4cccc5cccc(c(c1)c23)c54
perylene
O=C1CCC(=O)O1
succinic anhydride
[Al+3].[Cl-].[Cl-].[Cl-]
aluminum chloride
O=C(O)CCC(=O)c1ccc2cccc3c4cccc5cccc(c1c23)c54
brownish solid
Rendimiento 100.2%
O=C(O)CCC(=O)c1ccc2cccc3c4cccc5cccc(c1c23)c54
γ-oxo-4-(perylen-1-yl)butanoic acid
Rendimiento 100.2%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe substance obtained here
  2. 2
    Otrowas immersed in an ice bath
  3. 3
    Otrothe 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
    OtroThe solid substance obtained here
  8. 8
    Filtraciónwas collected by filtration
  9. 9
    workup.ADDITIONThis solid substance was dispersed in 100 ml of xylene
  10. 10
    Temperaturawas heated to 140° C.
  11. 11
    Extracciónto extract the impurities
  12. 12
    TemperaturaAfter the substance was cooled slowly back to room temperature
  13. 13
    Filtraciónthe solid substance was collected by filtration
  14. 14
    Otrowas dried under reduced pressure

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08475685B2uspto-grants-2013_07