Hexahydrophthalic anhydride → HCID 2756601, compound

HRID 1496833Notes

Reaction equation

HRID 1496833 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[CH:3]2[CH2:7][CH2:8][CH2:9][CH2:10][CH:2]12.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[C:4]([CH:3]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:2]1[C:1]([OH:6])=[O:11])(=[O:5])[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=1

Participants

4

Reactant 2

HCID 85689Hexahydrophthalic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2756601HCID 2756601, compoundYield 113.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a 2.5 l sulfuration flask equipped with a mechanical stirrer, thermometer and a refrigerator, 154.17 g (0.5 mol) of hexahydrophtalic anhydride are dissolved in 800 ml of benzene. The solution is cooled in an ice bath and 133.34 g (1.1 mol) of AlCl3 are added portion wise over one hour while maintaining the temperature between 0° C. and 5° C. When the addition is complete, the ice bath is removed and the reaction mixture is stirred for 2 hours at room temperature and subsequently heated to reflux during one hour. After cooling to room temperature, the reaction mixture is poured onto a mixture of ice and water while stirring with a mechanical stirrer. The precipitated product is filtered off and washed several times with water until the pH of the wash water is neutral. The material is dried in vacuum and the remaining product dissolved in chloroform. The solution is filtered over hyflo and the volume of the filtrate reduced in vacuum. The product precipitates as an off-white solid that is filtered off, washed with additional solvent and dried in vacuum. 66 g (57% yield) of the product are obtained as a white solid with a melting point of 130-132° C. 1H-NMR analysis is in agreement with the presence of a compound possessing the cis configuration of the substituents on the cyclohexane ring.

Workup

  1. customIn a 2.5 l sulfuration flask equipped with a mechanical stirrer
  2. temperatureThe solution is cooled in an ice bath
  3. temperaturewhile maintaining the temperature between 0° C. and 5° C
  4. additionWhen the addition
  5. customthe ice bath is removed
  6. temperaturesubsequently heated
  7. temperatureto reflux during one hour
  8. temperatureAfter cooling to room temperature
  9. additionthe reaction mixture is poured onto a mixture of ice and water
  10. stirringwhile stirring with a mechanical stirrer
  11. filtrationThe precipitated product is filtered off
  12. washwashed several times with water until the pH of the wash water
  13. customThe material is dried in vacuum
  14. dissolutionthe remaining product dissolved in chloroform
  15. filtrationThe solution is filtered over hyflo
  16. customThe product precipitates as an off-white solid
  17. filtrationthat is filtered off
  18. washwashed with additional solvent
  19. customdried in vacuum

Sources & evidence

ORD record
ord-7695e8b05aaf4aa7b4824ede51ba4e5d
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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