Benzenebutanol → 4-Phenylbutanal

HRID 878

反応式

HRID 878 の反応式
[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

参加物

6

反応物 3

HCID 76889BenzenebutanolHCID 178418287HCID 178418287、化合物HCID 178418299HCID 178418299、化合物

生成物 1

HCID 290304-Phenylbutanal収率 22.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-acafbcbe9a2a44309d2b4dd92b3f58bb
出典データセット
uspto-grants-1998_03
特許番号
US05723459

関連ノート

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