Isopropanol → cis-3-Allylcyclohexanol

HRID 854664Notes

Reaction equation

HRID 854664 reaction equation
[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]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8058HexaneHCID 22042274Lithium diisobutylaluminum hydride

Product 1

HCID 58763359cis-3-Allylcyclohexanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c97a9587b71e4b388a55597e8c213e13
Source dataset
uspto-grants-2007_08
Patent number
US07259177B2

Reaction notes

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