1-Chloroanthraquinone → 9,10-Anthracenedione, 1-(phenylthio)-

HRID 1946222Notes

Reaction equation

HRID 1946222 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:9]1[C:22]2[C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>C(OC(O)C)C>[C:1]1([S:7][C:16]2[C:15]3[C:14](=[O:24])[C:13]4[C:22](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:21](=[O:23])[C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 67091-ChloroanthraquinoneHCID 7969ThiophenolHCID 11430Potassium Carbonate

Product 1

HCID 259059,10-Anthracenedione, 1-(phenylthio)-Yield 96%

Reagents, catalysts & solvents 1

HCID 101298981-EthoxyethanolSolvent

Conditions

Temperature
120 °C

Procedure

45 g Thiophenol are added dropwise to a suspension of 100 g 1-chloro-anthraquinone and 63 g potassium carbonate in 150 ml ethoxyethanol at 23° C. under stirring. The reaction is strongly exotherm and addition must be performed very slowly, and subsequent addition of solvent improves fluidity and stirring of the reaction mixture. After heating at 120° C. for 3½ hours and subsequent cooling to 23° C., the mixture is filtered on glass (porosity 3) to afford a presscake which is washed with 1 l of methanol. The presscake is in turn suspended in 1 l water at 50° C. and again filtered on a glass filter (porosity 3). Further washing of the presscake with warm water (4 l) affords a filtrate of neutral pH. The presscake is finally dried at 60° C./5·103 Pa for 12 hours to provide 124.1 g of powdery orange 1-phenylsulfanyl-anthraquinone of formula

Workup

  1. additionaddition
  2. additionsubsequent addition of solvent
  3. stirringstirring of the reaction mixture
  4. temperaturesubsequent cooling to 23° C.
  5. filtrationthe mixture is filtered on glass (porosity 3)
  6. customto afford a presscake which
  7. washis washed with 1 l of methanol
  8. customsuspended in 1 l water at 50° C.
  9. filtrationagain filtered on a glass
  10. filtrationfilter (porosity 3)
  11. washFurther washing of the presscake with warm water (4 l)
  12. customaffords a filtrate of neutral pH
  13. customThe presscake is finally dried at 60° C./5·103 Pa for 12 hours

Sources & evidence

ORD record
ord-74a829dea8ef4e56b9150966d347e0e0
Source dataset
uspto-grants-2013_03
Patent number
US08399161B2

Reaction notes

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