Isopropanol → cis-3-Allylcyclohexanol

HRID 347412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347412
[H-].C([Al+]CC(C)C)C(C)C.[Li+].[H-].C(O)(C)C.[CH2:17]([CH:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1)[CH:18]=[CH2:19]>CCCCCC.C(OCC)C>[CH2:17]([C@@H:20]1[CH2:25][CH2:24][CH2:23][C@H:22]([OH:26])[CH2:21]1)[CH:18]=[CH2:19]

Komponenten

6

Edukt 3

HCID 3776IsopropanolHCID 112980033-AllylcyclohexanoneHCID 22042274Lithium diisobutylaluminum hydride

Produkt 1

HCID 58763359cis-3-Allylcyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

87 ml of a 1 molar solution of lithium diisobutylaluminum hydride in n-hexane are dissolved in 100 ml of diethyl ether, and 7 ml of isopropanol are added at 0° C. After the evolution of gas has ended, 12.4 g of 3-allylcylohexanone, dissolved in 50 ml of diethyl ether, are added. The mixture is stirred at room temperature for 48 hours. The reaction mixture is quenched by addition of 1M hydrochloric acid and the aqueous phase is saturated with sodium chloride and extracted five times with in each case 200 ml of ethyl acetate. The combined organic phases are washed with 2N sodium hydroxide solution and dried over magnesium sulfate, and the solvent is then removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=15:1=>5:1. This gives 6.8 g of cis-3-allylcyclohexanol as an oil. C9H16O (140.23), MS(ESI): 141 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.22.

Aufarbeitung

  1. additionare added
  2. customThe reaction mixture is quenched by addition of 1M hydrochloric acid
  3. extractionextracted five times with in each case 200 ml of ethyl acetate
  4. washThe combined organic phases are washed with 2N sodium hydroxide solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is then removed under reduced pressure
  7. customThe residue is purified on silica gel using the mobile phase n-heptane

Quellen und Nachweise

ORD-Eintrag
ord-8500f8da4ab54cee8075fcc28fb348a6
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173151B2

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