Benzenebutanol → 4-Phenylbutanal

HRID 53559

반응식

HRID 53559 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cr](Cl)([O-])(=O)=O.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl.CCOCC>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 76889BenzenebutanolHCID 178418287HCID 178418287, 화합물HCID 178418299HCID 178418299, 화합물

생성물 1

HCID 290304-Phenylbutanal수율 22.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3.2 mL (20.8 mmol) of 4-phenyl-1-butanol (Aldrich Chemical Co.) in 20 mL of CH2Cl2 at 0° C. was added 3.2 g of powdered 3 Å molecular sieves and then 5.37 g (24.9 mmol) of pyridinum chlorochromate (PCC). The resulting suspension was stirred at 0° C. for 1 h at which time an additional 2.16 g (10.0 mmol) of PCC was added and the reaction mixture was warmed to room temperature. After stirring at ambient temperature for 0.5 h, the reaction mixture was diluted with ether and filtered through celite to give 2.5 g of the crude product. Flash chromatography (elution with 5% ethyl acetate in hexane) yielded 700 mg of the aldehyde 119. 1H NMR was consistent with the structure.

후처리

  1. additionwas added
  2. filtrationfiltered through celite
  3. customto give 2.5 g of the crude product
  4. washFlash chromatography (elution with 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-4563dea700904bf38ba21d38dbfaeda7
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620971

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