Isopropanol → cis-3-Allylcyclohexanol

HRID 854664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 854664
[H-].C([Al+]CC(C)C)C(C)C.[Li+].[H-].[CH:13]([OH:16])([CH3:15])[CH3:14].[CH3:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(OCC)C>[CH2:19]([C@@H:20]1[CH2:21][CH2:22][CH2:15][C@H:13]([OH:16])[CH2:14]1)[CH:18]=[CH2:17]

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 8058HexaneHCID 22042274Lithium diisobutylaluminum hydride

Produkt 1

HCID 58763359cis-3-Allylcyclohexanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

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 ceased, 12.4 g of cis-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 HCl 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 NaOH and dried over MgSO4, 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. C9H160 (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 HCl
  3. extractionextracted five times with in each case 200 ml of ethyl acetate
  4. washThe combined organic phases are washed with 2N NaOH
  5. dry with materialdried over MgSO4
  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-c97a9587b71e4b388a55597e8c213e13
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259177B2

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