1,5-Dichloroanthraquinone → HCID 23089723, compound

HRID 1726837Notes

Reaction equation

HRID 1726837 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-:12].[K+].Cl[C:15]1[C:28]2[C:27](=[O:29])[C:26]3[C:21](=[C:22](Cl)[CH:23]=[CH:24][CH:25]=3)[C:20](=[O:31])[C:19]=2[CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.CN(C=O)C.[Cu]>[C:1]1([O:11][C:15]2[C:28]3[C:27](=[O:29])[C:26]4[C:21](=[C:22]([O:12][C:9]5[C:10]6[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=6)[CH:6]=[CH:7][CH:8]=5)[CH:23]=[CH:24][CH:25]=4)[C:20](=[O:31])[C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 67111,5-DichloroanthraquinoneHCID 70051-NaphtholHCID 14797Potassium Hydroxide2×

Product 1

HCID 23089723HCID 23089723, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 50 parts of 1-naphthol and 17 parts of potassium hydroxide were dissolved in 500 parts of toluene, and the mixture was refluxed under heat. After stirred for 4 hours, the solution was allowed to cool, and the precipitated solid was filtered. Then, under a nitrogen stream, the precipitate obtained, 24 parts of 1,5-dichloroanthraquinone and 7.2 parts of copper powder were dissolved in 500 parts of DMF, and the mixture was refluxed under heat for 5 hours. The reaction solution poured into an aqueous potassium hydroxide solution, and the precipitated solid was filtered, washed, and dried. Then, after removal of inorganic materials with toluene, the solid obtained was recrystallized from 2-ethoxyethanol, filtered, washed, and dried, to give 21 parts of 1,5-bis(1-naphthyloxy)anthraquinone as an intermediate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat
  3. temperatureto cool
  4. filtrationthe precipitated solid was filtered
  5. customThen, under a nitrogen stream, the precipitate obtained
  6. temperaturethe mixture was refluxed
  7. temperatureunder heat for 5 hours
  8. filtrationthe precipitated solid was filtered
  9. washwashed
  10. customdried
  11. customThen, after removal of inorganic materials with toluene
  12. customthe solid obtained
  13. customwas recrystallized from 2-ethoxyethanol
  14. filtrationfiltered
  15. washwashed
  16. customdried

Sources & evidence

ORD record
ord-e0464c2ecdbe4913ad845115f068017c
Source dataset
uspto-grants-2009_02
Patent number
US07494721B2

Reaction notes

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