Hydrochloric Acid → 3,6-Dibenzoyl-9-methylcarbazole

HRID 363279Notes

Reaction equation

HRID 363279 reaction equation
[CH3:1][N:2]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[Al+3].[Cl-].[Cl-].[Cl-].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>ClC(Cl)C>[C:19]([C:11]1[CH:12]=[CH:13][C:14]2[N:2]([CH3:1])[C:3]3[C:8]([C:9]=2[CH:10]=1)=[CH:7][C:6]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:5][CH:4]=3)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 15142N-MethylcarbazoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 544921453,6-Dibenzoyl-9-methylcarbazole

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

67.0 g (0.37 mol) of 9-methylcarbazole were dissolved in 400 ml of dry dichloroethane, to which 105.0 g (0.79 mol) of AlCl3 were added. 104.0 g (0.74 mol) of benzoyl chloride were added dropwise with stirring and cooling with ice. Stirring was continued for another 3 hours at room temperature, and the reaction mixture was then decomposed with ice and hydrochloric acid and the organic phase was washed to neutrality with water and NaHCO3 solution. The remaining water was removed by azeotropic distillation. The dichloroethane solution was concentrated, whereupon the diketone crystallized out. It was recrystallized once more from dichloroethane; m.p. 222° C.; (Lit. 16): m.p. 2190° C.), colorless crystals. Yield: 114.2 g (79.3%).

Workup

  1. additionwere added
  2. temperaturecooling with ice
  3. stirringStirring
  4. washthe organic phase was washed
  5. customThe remaining water was removed by azeotropic distillation
  6. concentrationThe dichloroethane solution was concentrated, whereupon the diketone
  7. customcrystallized out
  8. customIt was recrystallized once more from dichloroethane

Sources & evidence

ORD record
ord-3c4017fbfcec452f9557d65ecb5fd659
Source dataset
uspto-grants-1999_02
Patent number
US05874179

Reaction notes

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