Sodium Sulfate → 1-Nitroanthraquinone

HRID 329579Notes

Reaction equation

HRID 329579 reaction equation
[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[CH2:14][CH:13]=[CH:12][CH2:11][C:10]=3[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[N+:1]([C:4]1[C:17]2[C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:19])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 19871023HCID 19871023, compound

Product 1

HCID 67041-NitroanthraquinoneYield 91.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

15 g (58.8 mmol) of 1-nitro-5,8-dihydroanthraquinone and 20.45 g of manganese dioxide are stirred at reflux for 2 hours in 150 ml of methylene chloride. After addition of 15 g of anhydrous sodium sulfate, the mixture is filtered hot and the residue is repeatedly extracted by boiling in methylene chloride. Concentration of the mother liquors by evaporation gives 13.58 g (91%) of crude 1-nitroanthraquinone (melting point: 225°-230° C.), which can be recrystallised from toluene (melting point: 228°-232° C.).

Workup

  1. filtrationthe mixture is filtered hot
  2. extractionthe residue is repeatedly extracted
  3. customConcentration of the mother liquors by evaporation

Sources & evidence

ORD record
ord-b7e82a7f83344170889e1b18f601bbf7
Source dataset
uspto-grants-1990_01
Patent number
US04892686

Reaction notes

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