Hydrochloric Acid → 2,5-Dihydroxyterephthalonitrile

HRID 342324

Reaktionsgleichung

Reaktionsgleichung von HRID 342324
[C:1]([C:3]1[CH:8]=[C:7]([O:9]C)[C:6]([C:11]#[N:12])=[CH:5][C:4]=1[O:13]C)#[N:2].[Br-].[Br-].[Br-].[Al+3].Cl>C1C=CC=CC=1>[C:1]([C:3]1[CH:8]=[C:7]([OH:9])[C:6]([C:11]#[N:12])=[CH:5][C:4]=1[OH:13])#[N:2]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 166749BromhydrolHCID 125452802,5-Dimethoxyterephthalonitrile

Produkt 1

HCID 6433912,5-DihydroxyterephthalonitrileAusbeute 41,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

In a 5 liter-reaction vessel, 100 g (5.32×10-1M) of 2,5-dicyano-1,4-dimethoxybenzene, 312.5 g (1.17M) of anhydrous aluminum tribromide and 2.5 liters of dry benzene were placed, followed by heat-refluxing for 7 hours. After the reaction, the reaction mixture as cooled and poured into a mixture of 3 kg of crushed ice and 500 ml of concentrated hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration and dissolved in 2N-sodium hydroxide aqueous solution. The resultant insoluble residue was filtered off and the filtrate was acidified with 2N-hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration and washed with water, followed by drying to obtain 35.5 g of 2,5-dicyanohydroquinone (Yield: 41.7%).

Aufarbeitung

  1. temperatureby heat-refluxing for 7 hours
  2. customAfter the reaction
  3. temperaturethe reaction mixture as cooled
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. dissolutiondissolved in 2N-sodium hydroxide aqueous solution
  7. filtrationThe resultant insoluble residue was filtered off
  8. customto precipitate a crystal
  9. filtrationThe crystal was recovered by filtration
  10. washwashed with water
  11. customby drying

Quellen und Nachweise

ORD-Eintrag
ord-e24c3e1f4a2442379c2b2c8680fe1f38
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05858269

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