Hydrogen Peroxide → 3,5-Dimethyl-4-nitrophenol

HRID 1931902

Reaktionsgleichung

Reaktionsgleichung von HRID 1931902
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([CH3:10])[C:7]=1[N:8]=[O:9].[OH:12]O>C(O)(=O)C.N.N.N.N.N.N.O.O.O.O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O>[CH3:10][C:6]1[CH:5]=[C:4]([OH:11])[CH:3]=[C:2]([CH3:1])[C:7]=1[N+:8]([O-:12])=[O:9]

Komponenten

5

Edukt 2

HCID 784Hydrogen Peroxide2×HCID 2360193,5-Dimethyl-4-nitrosophenol

Produkt 1

HCID 1384663,5-Dimethyl-4-nitrophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 16211167Ammonium paramolybdate tetrahydrateKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 3,5-dimethyl-4-nitrosophenol (70.63 g) from above and (NH4)6Mo7O24.4H2O) (2.83g) in 770 ml of glacial acetic acid was warmed to 100° C. 30% H2O2 (84 ml) was added to the mixture in 10 ml portions until an exothermic reaction was observed. The reaction mixture was then stirred and the remainder of the H2O2 solution added in small portions. The reaction mixture was heated and stirred until a clear dark red solution results. A yellow-orange solid precipitated from the solution after stirring for another 20-30 minutes. The reaction mixture was stirred overnight and filtered to give a small amount of a yellow solid and a clear dark red filtrate. The red filtrate was concentrated in vacuo and partitioned between water and ether. The aqueous layer was washed with ether and the combined ether extracts washed with 10% sodium carbonate until the aqueous layer becomes basic. The ether extract was dried over anhydrous sodium sulfate, filtered, concentrated and allowed to cool overnight. After cooling in an ice bath the mixture was filtered to give 49.5 g of 3,5-dimethyl-4-nitrophenol as a yellow-green solid. Mp. 106-108° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. stirringstirred until a clear dark red solution
  3. customresults
  4. customA yellow-orange solid precipitated from the solution
  5. stirringafter stirring for another 20-30 minutes
  6. stirringThe reaction mixture was stirred overnight
  7. filtrationfiltered
  8. customto give a small amount of a yellow solid
  9. concentrationThe red filtrate was concentrated in vacuo
  10. custompartitioned between water and ether
  11. washThe aqueous layer was washed with ether
  12. washthe combined ether extracts washed with 10% sodium carbonate until the aqueous layer
  13. extractionThe ether extract
  14. dry with materialwas dried over anhydrous sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated
  17. temperatureto cool overnight
  18. temperatureAfter cooling in an ice bath the mixture
  19. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-ee43fa520fd84ad294a477c721be727e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188314B2

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