1-(4-Biphenyl)-1-propanol → p-Phenylpropiophenone

HRID 1485088노트

반응식

HRID 1485088 반응식
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]([CH:7]([OH:10])[CH2:8][CH3:9])=[CH:3][CH:2]=1>C(OCC)C.[O-2].[Mn+4].[O-2]>[C:1]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:2]=[CH:3][C:4]([C:7](=[O:10])[CH2:8][CH3:9])=[CH:5][CH:6]=1

참가 물질

4

반응물 1

HCID 131304821-(4-Biphenyl)-1-propanol

생성물 1

HCID 95230p-Phenylpropiophenone수율 73.2%

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

To a solution in diethyl ether (30.0 mL) of the compound (1.27 g) obtained in step (1) above, manganese(IV) oxide (9.57 g) was added and the mixture was stirred at room temperature for 45 hours. After removing the insoluble matter by filtration, the filtrate was concentrated under reduced pressure. To a solution of the resulting residue in acetone (60.0 mL), a Jones' reagent {see Org. Synth., Coll. Vol. VI, 542 (1988)}(1.20 mL) was added until the color of the Jones' reagent was yet to disappear. The reaction mixture was concentrated under reduced pressure and ethyl acetate and water were added to the residue. Extraction with ethyl acetate was conducted three times and the combined organic layers were washed with saturated brine. After passage through a phase separator, the washed organic layers were concentrated under reduced pressure. The resulting residue was recrystallized with n-hexane to give the titled compound as a colorless solid (921 mg).

후처리

  1. customAfter removing the insoluble matter
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionVol. VI, 542 (1988)}(1.20 mL) was added until the color of the Jones' reagent
  5. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate and water
  6. additionwere added to the residue
  7. extractionExtraction with ethyl acetate
  8. washthe combined organic layers were washed with saturated brine
  9. concentrationAfter passage through a phase separator, the washed organic layers were concentrated under reduced pressure
  10. customThe resulting residue was recrystallized with n-hexane

출처 및 근거

ORD 기록
ord-fa03332dda2e4c59880616176888c9fe
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422240B2

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