Phenol → 1,8-Diphenoxyanthraquinone

HRID 127167

Reaktionsgleichung

Reaktionsgleichung von HRID 127167
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:8].[K+].Cl[C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[N+]([O-])=O)[C:16](=[O:29])[C:15]=2[CH:14]=[CH:13][CH:12]=1>>[O:7]([C:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][C:21]=3[O:8][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:16](=[O:29])[C:15]=2[CH:14]=[CH:13][CH:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 3

HCID 996PhenolHCID 14797Potassium HydroxideHCID 2257041-Nitro-8-chloroanthraquinone

Produkt 1

HCID 665011,8-Diphenoxyanthraquinone

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 21 g. phenol, 13 g. potassium hydroxide and 270 g. o-chlorotoluene was converted to a water-free slurry of potassium phenoxide by azeotropic distillation of all the water formed. After cooling back to 100° C., 28.8 g. of 1-chloro-8-nitroanthraquinone was charged and the whole heated and stirred at 130° C. for 6 hours. The product was isolated by steam distillation, filtration, washing and drying. A 37.7 g. yield (96.2% of theory) of a product identical to authentic 1,8-diphenoxyanthraquinone in a thin layer chromatogram and free of starting material was obtained.

Aufarbeitung

  1. additionA mixture of 21 g
  2. distillationo-chlorotoluene was converted to a water-free slurry of potassium phenoxide by azeotropic distillation of all the water
  3. customformed
  4. temperaturethe whole heated
  5. customThe product was isolated by steam distillation, filtration
  6. washwashing
  7. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-a1f80f2135794476b69ab2f82b7dcaa3
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04255342

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