5-Phenyl-1-pentanol → Cyclohexanepentanol

HRID 846247ノート

反応式

HRID 846247 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C>[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][OH:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

3

反応物 1

HCID 615235-Phenyl-1-pentanol

生成物 1

HCID 269450Cyclohexanepentanol

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To a portion of 100 mL glacial acetic acid, purged with argon, was added 5.62 g of PtO2 (Aldrich) followed by a solution of 25.00 g (152.2 mmol, Aldrich) of 5-phenyl-1-pentanol in 100 mL glacial acetic acid. The reaction vessel was evacuated and purged with H2 three times, the the reaction mixture was stirred under H2 (1 atm) of 22 hours. The reaction was not complete by thin layer chromatography. A second portion of 3.25 (Aldrich) of PtO2 was added and the reaction was stirred under H2 (1 atm) for an additional 32 hours. The mixture was filtered through a 0.4 μM polycarbonate filter, the filtrate was concentrated in vacuo and then azeotroped four times with toluene to give 28.08 g (164.9 mmol, 100%) of a cloudy liquid. 1H NMR indicated the crude material was about a 2:1 mixture of the alcohol title compound and the corresponding acetate.

後処理

  1. customTo a portion of 100 mL glacial acetic acid, purged with argon
  2. additionwas added 5.62 g of PtO2 (Aldrich)
  3. customThe reaction vessel was evacuated
  4. custompurged with H2 three times
  5. additionA second portion of 3.25 (Aldrich) of PtO2 was added
  6. stirringthe reaction was stirred under H2 (1 atm) for an additional 32 hours
  7. filtrationThe mixture was filtered through a 0.4 μM polycarbonate
  8. filtrationfilter
  9. concentrationthe filtrate was concentrated in vacuo
  10. customazeotroped four times with toluene
  11. customto give 28.08 g (164.9 mmol, 100%) of a cloudy liquid

出典と根拠

ORDレコード
ord-edf0c6166a164e6f89b65e816177430a
出典データセット
uspto-grants-1992_08
特許番号
US05135939

反応ノート

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