4-Pentylcyclohexanecarboxylic Acid → (4-Pentylcyclohexyl)methanol

HRID 48103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 48103
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:12]1[CH2:17][CH2:16][CH:15]([C:18](O)=[O:19])[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]>C(OCC)C>[CH2:7]([CH:12]1[CH2:13][CH2:14][CH:15]([CH2:18][OH:19])[CH2:16][CH2:17]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Komponenten

4

Edukt 2

HCID 988824-Pentylcyclohexanecarboxylic AcidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 13548135(4-Pentylcyclohexyl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a slurry of lithium aluminum hydride (2 equi.) in diethyl ether (4 mL/mmole), a solution of commercially available 4-pentylcyclohexanecarboxylic acid (20) (1 equi.) in diethyl ether (3 ml/mmole) was added at ice temperature over a period of 20 min. The reaction mixture was stirred at room temperature for 24 h, cooled to ice temperature, quenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) consecutively. MgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture, stirred for 30 min, filtered through celite, and concentrated in vacuo to give (4-pentyl-cyclohexyl)-methanol (21) a colorless oil (95%).

Aufarbeitung

  1. temperaturecooled to ice temperature
  2. customquenched slowly with water (1 mL/g LAH), 15% aqueous sodium hydroxide (1 mL/g LAH), and water (3 mL/g LAH) consecutively
  3. additionMgSO4 (5 g/100 mL reaction solution) was added to the reaction mixture
  4. stirringstirred for 30 min
  5. filtrationfiltered through celite
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2256d365504d43788de3c8eed709f31c
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06703082B1

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