Phenol → 1,8-Diphenoxyanthraquinone

HRID 127167

Reaction equation

HRID 127167 reaction equation
[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

Participants

4

Reactant 3

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

Product 1

HCID 665011,8-Diphenoxyanthraquinone

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1f80f2135794476b69ab2f82b7dcaa3
Source dataset
uspto-grants-1981_03
Patent number
US04255342

Linked notes

Loading…