3-Nitrotoluene → 2,2'-Dimethylbenzidine

HRID 1768510

Reaktionsgleichung

Reaktionsgleichung von HRID 1768510
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH-].[Na+]>[Zn].C(O)C>[CH3:10][C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][C:7]=1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][C:6]=1[CH3:10]

Komponenten

5

Edukt 2

HCID 74223-NitrotolueneHCID 14798Sodium Hydroxide

Produkt 1

HCID 665372,2'-Dimethylbenzidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator2×HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 40.0 grams, 0.30 moles, of m-nitrotoluene; 24 mL of a 20 percent aqueous solution of sodium hydroxide, and 120 mL ethanol is stirred and heated at gentle reflux. Zinc dust, 69.6 grams, is slowly added to keep the solution boiling without heating. Following addition of the zinc dust, the mixture is heated at reflux for about 4 hours. The hot mixture is filtered by suction, and the zinc residue is washed with ethanol. Concentrated hydrochloric acid is then slowly added to the filtrate. The precipitate formed is collected following filtration and redissolved in hot water. The aqueous solution is thereafter allowed to cool to room temperature and basified with a 20 percent aqueous solution of sodium hydroxide. The resulting DMB is an oil that is extracted with ethyl ether following its formation. Subsequent evaporation of the ethyl ether yields an oil containing 18.3 grams, 57.4 percent, of solids following cooling. Finally, the solid DMB is recrystallized from ethyl ether.

Aufarbeitung

  1. additionA mixture of 40.0 grams, 0.30 moles
  2. temperatureheated at gentle reflux
  3. temperaturewithout heating
  4. temperaturethe mixture is heated
  5. temperatureat reflux for about 4 hours
  6. filtrationThe hot mixture is filtered by suction
  7. washthe zinc residue is washed with ethanol
  8. additionConcentrated hydrochloric acid is then slowly added to the filtrate
  9. customThe precipitate formed
  10. customis collected
  11. filtrationfiltration
  12. dissolutionredissolved in hot water
  13. extractionis extracted with ethyl ether following its formation
  14. customSubsequent evaporation of the ethyl ether
  15. customyields an oil
  16. additioncontaining 18.3 grams, 57.4 percent
  17. temperatureof solids following cooling
  18. customFinally, the solid DMB is recrystallized from ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-60b78d983f994b53950b7f40a0dc54bc
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05378420

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