Benzene → Phenol

HRID 1723501

Reaktionsgleichung

Reaktionsgleichung von HRID 1723501
C1C=CC=CC=1.FC(F)(F)C(OO)=O.CCCCCCCC.[F:23][C:24]([F:35])([F:34])[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>FC(F)(F)C(O)=O.C([O-])(=O)C.[Co+2].C([O-])(=O)C.O>[F:23][C:24]([F:34])([F:35])[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26].[C:28]1([OH:27])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

9

Edukt 4

HCID 241Benzene2×HCID 356OctaneHCID 68143Acetic acid, 2,2,2-trifluoro-, phenyl esterHCID 10290812Trifluoroperacetic acid

Produkt 2

HCID 996PhenolHCID 68143Acetic acid, 2,2,2-trifluoro-, phenyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6277Cobalt diacetateKatalysatorHCID 962WaterLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel3×

Versuchsvorschrift

To a solution of benzene (0.428 g, 5.49 mmol) and cobalt(II) acetate (0.179 g, 1.01 mmol) in 50 mL of trifluoroacetic acid/10% trifluoroacetic anhydride at 25° C. was added 10 mL of a 0.5M solution of trifluoroperacetic acid in trifluoroacetic acid/10% trifluoracetic anhydride (cooled to 0° C.) by syringe pump over 20 h with stirring. The reaction mixture was initially a reddish-pink color which turned to dark green-black upon addition of the peracid. After the addition was complete, the reaction mixture was stirred an additional 7 h, then analyzed by gas chromatography using n-octane as an internal standard. The yield of phenyl trifluoroacetate was 56%, with a 58% conversion of benzene (selectivity to phenyl trifluoroacetate=96%). Addition of water to the reaction mixture resulted in the quantitative conversion of phenyl trifluoroacetate to phenol and trifluoroacetic acid solvent.

Aufarbeitung

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred an additional 7 h

Quellen und Nachweise

ORD-Eintrag
ord-81c2fa59cb5349f0a6a66f6a4247e520
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04861911

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