Hydrogen Bromide → 4,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

HRID 2225980

Reaktionsgleichung

Reaktionsgleichung von HRID 2225980
F[C:2](F)(F)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[F:13][C:14]([F:20])([F:19])S(O)(=O)=O.[C:21]1([O:27]C)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Br>C(O)(=O)C>[OH:27][C:21]1[CH:26]=[CH:25][C:2]([C:3]([C:24]2[CH:23]=[CH:22][C:21]([OH:27])=[CH:26][CH:25]=2)([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:14]([F:20])([F:19])[F:13])=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 260Hydrogen BromideHCID 7519AnisoleHCID 99052,2,2-TrifluoroacetophenoneHCID 62406Trifluoromethanesulfonic acid

Produkt 1

HCID 190051754,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 100 grams (0.57 mol) of trifluoroacetophenone, 100 grams (0.7 mol) trifluoromethane sulfonic acid, and 100 grams (10.9 mol) anisole is stirred at room temperature for 24 hours. The mixture is then transferred to a separatory funnel and the organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml). The organic phase is dried and the volatiles removed in vacuo. The resulting material is crystallized from aqueous methanol. 37.2 grams (0.1 mol) of this product is refluxed with glacial acetic acid saturated with anhydrous hydrobromic acid. The mixture is cooled and poured over crushed ice and the solid collected. The crude material is recrystallized from ethanol and petroleum ether to give 1,1-bis(4-hydroxyphenyl)-l-phenyl-2,2,2-trifluoroethane.

Aufarbeitung

  1. customThe mixture is then transferred to a separatory funnel
  2. washthe organic material is washed with water (3×11), saturated bicarbonate (3×500 ml) and water (2×500 ml)
  3. customThe organic phase is dried
  4. customthe volatiles removed in vacuo
  5. customThe resulting material is crystallized from aqueous methanol
  6. temperatureThe mixture is cooled
  7. additionpoured
  8. customover crushed ice
  9. customthe solid collected
  10. customThe crude material is recrystallized from ethanol and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-92c0a08ba387428dad302770d73f7f57
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344981

Verknüpfte Notizen

Wird geladen…