Benzene → Phenol

HRID 1723501

반응식

HRID 1723501 반응식
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

참가 물질

9

반응물 4

HCID 241Benzene2회HCID 356OctaneHCID 68143Acetic acid, 2,2,2-trifluoro-, phenyl esterHCID 10290812Trifluoroperacetic acid

생성물 2

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

시약·촉매·용매 3

HCID 6277Cobalt diacetate촉매HCID 962Water용매HCID 6422Trifluoroacetic acid용매3회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-81c2fa59cb5349f0a6a66f6a4247e520
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04861911

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