Diethyl Ether → 1-Allyl-1-cyclohexanol

HRID 1596813Notes

Reaction equation

HRID 1596813 reaction equation
[CH2:1]([Li])CCC.[C:6]([C:10]([OH:18])([CH2:15][CH:16]=[CH2:17])[C:11]([CH3:14])(C)C)([CH3:9])(C)C.C1(=O)CCCCC1.C(OCC)C>CCCCC.C1COCC1.[Zn+2].[Br-].[Br-]>[CH2:15]([C:10]1([OH:18])[CH2:6][CH2:9][CH2:1][CH2:14][CH2:11]1)[CH:16]=[CH2:17]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 7967CyclohexanoneHCID 117899023-tert-butyl-2,2-dimethylhex-5-en-3-olHCID 178418339Butyllithium

Product 1

HCID 791451-Allyl-1-cyclohexanol

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.94 ml of a 1.4-molar solution of n-butyllithium (2.71 mmol) in pentane were added dropwise at 0° C. under argon for 2 minutes to a stirred solution of 500 mg (2.71 mmol) 3-tert-butyl-2,2-dimethylhex-5-en-3-ol in 4 ml THF. The solution obtained was stirred for 15 minutes, and then a solution of 610 mg (2.71 mmol) ZnBr2 in 2 ml THF and 280 μl (2.71 mmol) cyclohexanone were added. The reaction mixture was stirred for 4 hours and heated to room temperature. Subsequently, it was processed analogous to Example 1. The raw product obtained was cleaned by means of a silica column with 20% diethyl ether/light gasoline. There was obtained the alcohol as a colorless oil.

Workup

  1. customThe solution obtained
  2. stirringThe reaction mixture was stirred for 4 hours
  3. customThe raw product obtained

Sources & evidence

ORD record
ord-caa7db11a90040bcae87846bb6b1a124
Source dataset
uspto-grants-2001_09
Patent number
US06291713B1

Reaction notes

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