Acetic Acid → p,p'-(Phenylphosphinylidene)bisphenol

HRID 1760349

Reaktionsgleichung

Reaktionsgleichung von HRID 1760349
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:24])([C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.Br.C(O)(=O)C.C>C(O)C>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([P:9](=[O:24])([C:16]2[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 260Hydrogen Bromide2×HCID 297MethaneHCID 4589182Bis(4-methoxyphenyl)phenylphosphine oxide

Produkt 1

HCID 69930p,p'-(Phenylphosphinylidene)bisphenolAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of bis(4-methoxyphenyl)phenyl phosphine oxide (59.83 g, 0.1768 mol), 48% hydrobromic acid (400 ml, 3.536 mol), and glacial acetic acid (215 ml) was refluxed for 24 hrs. As the solution cooled to room temperature, the crude product remained in solution. The hydrobromic acid/glacial acetic acid mixture was added to stirred distilled water at room temperature to afford a light pink solid. The crude solid was washed several times in water and dried at ˜105° C. to afford 46.4 g (˜85% yield). The solid was dissolved in ethanol, treated with activated charcoal, and filtered through Celite 545. Distilled water was added to the stirred warm solution until a 50% aqueous ethanol solution was obtained. The mixture was then allowed to cool to ambient temperature. The product was recovered by filtration and dried under vacuum at 50° C. This recrystallization procedure was repeated an additional time to afford 22.66 g (41% yield) of a white solid, DSC (heating rate of 10° C./min) exotherm at 157° C. with sharp peaks at 227 and 233° C. [literature 233-234° C. (A. E. Senear, W. Valent, and J. Wirth J. Org. Chem. 25, 2001, 1960.)]

Aufarbeitung

  1. temperaturewas refluxed for 24 hrs
  2. distillationdistilled water at room temperature
  3. customto afford a light pink solid
  4. washThe crude solid was washed several times in water
  5. customdried at ˜105° C.
  6. customto afford 46.4 g (˜85% yield)
  7. filtrationfiltered through Celite 545
  8. additionDistilled water was added to the stirred
  9. temperaturewarm solution until a 50% aqueous ethanol solution
  10. customwas obtained
  11. temperatureto cool to ambient temperature
  12. filtrationThe product was recovered by filtration
  13. customdried under vacuum at 50° C
  14. customThis recrystallization procedure
  15. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-7be09c58ed774beb8867de5b1a5e4e6c
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06841652B2

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