Dodecane → N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidine

HRID 2106985

Reaktionsgleichung

Reaktionsgleichung von HRID 2106985
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[C:10]([CH3:15])[CH:9]=2)[CH:5]=[CH:4][C:3]=1[NH2:16].[OH-].[K+].CCCCC[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].I[C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1>[Cu](I)I.O>[CH3:38][C:35]1[CH:36]=[CH:37][C:32]([N:16]([C:28]2[CH:27]=[CH:26][C:25]([CH3:24])=[CH:30][CH:29]=2)[C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH:13]=[CH:12][C:11]([N:14]([C:13]4[CH:8]=[CH:9][C:10]([CH3:15])=[CH:11][CH:12]=4)[C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[C:10]([CH3:15])[CH:9]=3)=[CH:7][C:2]=2[CH3:1])=[CH:33][CH:34]=1

Komponenten

7

Edukt 4

HCID 8182DodecaneHCID 8413o-TolidineHCID 122074-Iodotoluene2×HCID 14797Potassium Hydroxide2×

Produkt 1

HCID 4396362N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidineAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysator2×HCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

In a round flask were charged 3.14 g (13.8 mmol) of o-tolidine, 40 g of potassium hydroxide, 400 mg of copper iodide, and 30 ml of n-dodecane, and the mixture was heated at 180° C. in a nitrogen stream. To the mixture was added dropwise 24.0 g (110 mmol) of 4-iodotoluene, and the heating at 180° C. was continued for 5 hours. Water was added to the reaction mixture, and the mixture was extracted with toluene. In order to assure completion of the reaction, the solvent was once removed by distillation, and 40 g of potassium hydroxide, 400 mg of copper iodide, and 24.0 g (110 mmol) of 4-iodotoluene were added to the residue, followed by allowing to react at 180° C. for 5 hours in a nitrogen stream. Water was added, and the mixture was extracted with toluene. The extract was dried over sodium sulfate and then treated with activated clay. The solvent was removed by distillation to obtain 5.98 g (yield: 75.7%) of N,N,N',N'-tetrakis-(4-methylphenyl)-3,3'-dimethylbenzidine, which was recrystallized from a mixed solvent of toluene/acetone/hexane to obtain 4.32 g (final yield: 54.7%) of a white crystal having a melting point of 174°-175° C. Analysis by high performance liquid chromatography revealed that the product has a high purity of 99.9%.

Aufarbeitung

  1. extractionthe mixture was extracted with toluene
  2. customcompletion of the reaction
  3. additionwere added to the residue
  4. customto react at 180° C. for 5 hours in a nitrogen stream
  5. extractionthe mixture was extracted with toluene
  6. dry with materialThe extract was dried over sodium sulfate
  7. additiontreated with activated clay
  8. customThe solvent was removed by distillation

Quellen und Nachweise

ORD-Eintrag
ord-2c670ec90ec94b80b144f59bd90e1013
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933245

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