Ethyl Acetate → 3-Cyclohexyl-1-propanol

HRID 27302

反応式

HRID 27302 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:13][CH2:14][C:15](O)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(OCC)(=O)C.[OH-].[Na+]>CCOCC.O>[CH:7]1([CH2:13][CH2:14][CH2:15][OH:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69702Cyclohexanepropanoic acidHCID 21226445Aluminium lithium hydride

生成物 1

HCID 707633-Cyclohexyl-1-propanol

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒2 回

実験手順

Lithium aluminum hydride (24.2 g, 0.64 mole) was slurried into 300 ml of dry ether (distilled from benzophenone ketyl, generated in situ from sodium and benzophenone). The slurry was cooled in an ice-water bath and a solution of 100 g (0.64 mole) of 3-cyclohexylpropionic acid (Bielstein 9:[2]13) in 250 ml of dry ether was slowly added. The resultant mixture was heated to reflux for 1 hr and then cooled in an ice-water bath. Ethyl acetate (100 ml) was slowly added to the mixture. This addition was followed by the addition of 24.2 ml of water, 24.2 ml of 15% aqueous sodium hydroxide solution and 72.6 ml of water. The mixture was filtered and the solvent was removed in vacuo. Distillation of this mixture at reduced pressure resulted in 71.6 g (78.7%) of pure 3-cyclohexylpropan-1-ol having the following physical characteristics:

後処理

  1. temperatureThe slurry was cooled in an ice-water bath
  2. temperatureto reflux for 1 hr
  3. temperaturecooled in an ice-water bath
  4. additionThis addition
  5. filtrationThe mixture was filtered
  6. customthe solvent was removed in vacuo
  7. distillationDistillation of this mixture at reduced pressure
  8. customresulted in 71.6 g (78.7%) of pure 3-cyclohexylpropan-1-ol having the following physical characteristics

出典と根拠

ORDレコード
ord-fa562def21a2426e86f38c41ef12a89a
出典データセット
uspto-grants-1980_09
特許番号
US04220795

関連ノート

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