Acetic Acid → 1,2,4,6-Tetraphenylpyridin-1-ium acetate

HRID 26573Notes

Reaction equation

HRID 26573 reaction equation
[C:1]1([C:7](=O)[CH:8]=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:33]([OH:36])(=[O:35])[CH3:34]>>[C:33]([O-:36])(=[O:35])[CH3:34].[C:27]1([N+:26]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:10][C:11]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 6115AnilineHCID 909792-Pentene-1,5-dione, 1,3,5-triphenyl-

Product 1

HCID 159202751,2,4,6-Tetraphenylpyridin-1-ium acetate

Procedure

In a suitable container (erlenmeyer flasks are suitable but any other vessel which may be heated could serve as well) place 33.33 g of recrystallized 1,3,5-triphenyl-2-penten-1,5-dione and 9.31 g of purified aniline. To this mixture add 37.5 ml of glacial acetic acid and heat on a steam bath or other suitable heating source for two hours. At the end of the heating period add 650 ml of distilled, deionized water and then add 6 N NaOH slowly with extremely rapid stirring. Discontinue the addition when the pH, indicated by a glass electrode, reaches 7.0. Allow any precipitate to settle, collect the supernate by filtration and retain this filtrate. Allow the filtrate to stand for a day, and then filter with 2 g of activated carbon by gravity through a tight filter paper to produce a decolorized filtrate. After determination of the 1,2,4,6-tetraphenylpyridinium acetate concentration (vide infra) dilute the solution to the desired concentration with distilled, deionized water. The 1,2,4,6-tetraphenylpyridinium cation is characterized through its perchlorate and perrhenate salts by elemental analysis.

Workup

  1. customIn a suitable container (erlenmeyer flasks are suitable
  2. temperatureany other vessel which may be heated could
  3. temperatureheat on a steam bath
  4. additionAt the end of the heating period add 650 ml
  5. distillationof distilled
  6. additiondeionized water and then add 6 N NaOH slowly with extremely rapid stirring
  7. additionthe addition when the pH
  8. customcollect the supernate
  9. filtrationby filtration
  10. waitto stand for a day
  11. filtrationfilter with 2 g of activated carbon by gravity through a tight filter paper
  12. customto produce a decolorized filtrate
  13. concentrationAfter determination of the 1,2,4,6-tetraphenylpyridinium acetate concentration (vide infra)
  14. additiondilute the solution to the desired
  15. concentrationconcentration
  16. distillationwith distilled

Sources & evidence

ORD record
ord-24c0bba72cee4fa2b7f843525056e36e
Source dataset
uspto-grants-1979_04
Patent number
US04150233

Reaction notes

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