Acetone → 2-Ethenyl-9H-carbazole

HRID 616805Notes

Reaction equation

HRID 616805 reaction equation
[C:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)(=O)[CH3:2].CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].CC(C)=O>C1(C)C(C)=CC=CC=1>[CH:1]([C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH:5]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 11143Aluminum isopropoxideHCID 2673322-Acetylcarbazole

Product 1

HCID 167279502-Ethenyl-9H-carbazole

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The monomer of this polymer is synthesized in accord with the procedures described by Hyde, Kricke and Ledwith in Polymers 14, 124 (1973). According to their method, a mixture of 24 grams 2-acetyl carbazole and 40 gram aluminum isopropoxide in 75 milliliters of xylene is heated to boiling under reflux conditions. Such heating is continued for three hours, during which time acetone forms within the mixture and is removed therefrom by distillation. Upon cooling, particulates (principally aluminum isopropoxide) are removed from the mixture by filtration and the filtrate collected in water. Upon standing, the xylene and aqueous layers separate, whereupon the xylene is drawn off and the aqueous layer subsequently extracted with three 60 milliliter portions of ether. The combined extracts are washed with water and dried over anhydrous magnesium sulfate (MgSO4 /NaOH). Evaporation of the ether yields 2-vinylcarbazole monomer.

Workup

  1. customThe monomer of this polymer is synthesized in accord with the procedures
  2. temperatureis heated
  3. temperatureSuch heating
  4. customis removed
  5. distillationby distillation
  6. temperatureUpon cooling
  7. customparticulates (principally aluminum isopropoxide) are removed from the mixture by filtration
  8. customthe filtrate collected in water
  9. customthe xylene and aqueous layers separate, whereupon the xylene
  10. extractionthe aqueous layer subsequently extracted with three 60 milliliter portions of ether
  11. washThe combined extracts are washed with water
  12. dry with materialdried over anhydrous magnesium sulfate (MgSO4 /NaOH)
  13. customEvaporation of the ether

Sources & evidence

ORD record
ord-89b2a27b550f4f919a01621381444e68
Source dataset
uspto-grants-1978_02
Patent number
US04076527

Reaction notes

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