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

Participants

Reaction Steps

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.

Provenance & Evidence