Potassium Persulfate → 1-Nitroanthraquinone

HRID 329581Notes

Reaction equation

HRID 329581 reaction equation
C([O-])(=O)C.[K+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[N+:18]([CH:21]1[C:34]2[C:33](=[O:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26](=[O:36])[C:25]=2[CH:24]=[CH:23][CH2:22]1)([O-:20])=[O:19]>O>[N+:18]([C:21]1[C:34]2[C:33](=[O:35])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26](=[O:36])[C:25]=2[CH:24]=[CH:23][CH:22]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 24412Potassium PersulfateHCID 517044Potassium AcetateHCID 19871025HCID 19871025, compound

Product 1

HCID 67041-NitroanthraquinoneYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With stirring, 0.38 part (3.89 mmol) of potassium acetate is dissolved in 5 parts of glacial acid at 90° C. Then 2.1 parts (7.77 mmol; 4 equivalents) of potassium persulfate are added, whereupon a white suspension forms. Then 1.0 g (3.84 mmol) of nitrodihydroanthraquinone is added. After stirring for 3 hours at 90° C., the mixture is cooled and poured into 50 ml of water. The precipitate is isolated by filtration, washed with water, and dried. The residue is extracted by boiling 3 times in toluene. Partial concentration of the mother liquors and subsequent cooling and filtration give 0.84 part (86% of theory) of 1-nitroanthraquinone with a melting point of 228°-230° C.

Workup

  1. stirringAfter stirring for 3 hours at 90° C.
  2. temperaturethe mixture is cooled
  3. customThe precipitate is isolated by filtration
  4. washwashed with water
  5. customdried
  6. extractionThe residue is extracted
  7. concentrationPartial concentration of the mother liquors
  8. temperaturesubsequent cooling
  9. filtrationfiltration

Sources & evidence

ORD record
ord-b0c0dcff660047f492cefe1d9b118ad7
Source dataset
uspto-grants-1990_01
Patent number
US04892686

Reaction notes

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