Toluene → HCID 23089721, compound

HRID 1726839Notes

Reaction equation

HRID 1726839 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:14].[K+].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][C:20]3[C:21]4[C:22](=[O:14])[C:16]5[C:21](=[C:20]([O:13][C:10]6[CH:9]=[CH:8][C:7]([C:1]7[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=7)=[CH:12][CH:11]=6)[CH:19]=[CH:18][CH:17]=5)[C:22](=[O:14])[C:16]=4[CH:17]=[CH:18][CH:19]=3)=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 71034-HydroxybiphenylHCID 14797Potassium Hydroxide

Product 1

HCID 23089721HCID 23089721, compound

Procedure

Under a nitrogen atmosphere, 4.3 parts of 4-phenylphenol and 1.5 parts of potassium hydroxide were dissolved in 80 parts of toluene and the solution was refluxed under heat. After stirred for 5 hours, the solution was allowed to cool, and the precipitated solid was filtered. Then, under a nitrogen stream, the precipitate, 2 parts of 1,5-dichloroanthraquinone and 0.6 part of copper powder were dissolved in 10 parts of DMF, and the mixture was refluxed under heat for 3 hours. The reaction solution was poured into an aqueous potassiumhydroxide 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 0.6 part of 1,5-bis(4-phenylphenoxy)anthraquinone as an intermediate.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heat
  3. temperatureto cool
  4. filtrationthe precipitated solid was filtered
  5. dissolutionThen, under a nitrogen stream, the precipitate, 2 parts of 1,5-dichloroanthraquinone and 0.6 part of copper powder were dissolved in 10 parts of DMF
  6. temperaturethe mixture was refluxed
  7. temperatureunder heat for 3 hours
  8. additionThe reaction solution was poured into an aqueous potassiumhydroxide solution
  9. filtrationthe precipitated solid was filtered
  10. washwashed
  11. customdried
  12. customThen, after removal of inorganic materials with toluene
  13. customthe solid obtained
  14. customwas recrystallized from 2-ethoxyethanol
  15. filtrationfiltered
  16. washwashed
  17. customdried

Sources & evidence

ORD record
ord-9b8d4a0ecddf4f1aa2cc428963ba0ff0
Source dataset
uspto-grants-2009_02
Patent number
US07494721B2

Reaction notes

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