Benzene → Phenol

HRID 2231783Notes

Reaction equation

HRID 2231783 reaction equation
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

Participants

9

Reactant 4

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

Product 2

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

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent3×

Procedure

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 0.5 M 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.

Workup

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

Sources & evidence

ORD record
ord-62d1f9dd09984d8baa1efa63fd08253c
Source dataset
uspto-grants-1988_11
Patent number
US04783550

Reaction notes

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