Toluene → HCID 23089725, compound

HRID 1726838Notes

Reaction equation

HRID 1726838 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[OH-:12].[K+].[C:14]1([CH3:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:18]1[C:19]2[C:20](=[O:12])[C:14]3[C:19](=[C:18]([O:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[CH:1]=4)[CH:17]=[CH:16][CH:15]=3)[C:20](=[O:12])[C:14]=2[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 86632-NaphtholHCID 14797Potassium Hydroxide

Product 1

HCID 23089725HCID 23089725, compound

Procedure

Under a nitrogen atmosphere, 50 parts of 2-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, 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 19 parts of 1,5-bis(2-naphthyloxy)anthraquinone as an intermediate.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat
  3. temperatureto cool
  4. filtrationthe precipitated solid was filtered
  5. dissolutionThen, under a nitrogen stream, the precipitate, 24 parts of 1,5-dichloroanthraquinone and 7.2 parts of copper powder were dissolved in 500 parts of DMF
  6. temperaturethe mixture was refluxed
  7. temperatureunder heat for 5 hours
  8. additionThe reaction solution poured into an aqueous potassium hydroxide 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-ba038de851bc440aaeae1cc2b0549dcc
Source dataset
uspto-grants-2009_02
Patent number
US07494721B2

Reaction notes

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