Cyclohexanone → 1-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanol

HRID 132104

Reaction equation

HRID 132104 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].CCCCC.Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1.[C:22]1(=[O:28])[CH2:27]CCC[CH2:23]1>O1CCCC1.[Cl-].[NH4+].C(OCC)(=O)C>[C:18]([C:14]1[CH:13]=[C:12]([C:22]2([OH:28])[CH2:27][CH2:3][C:1](=[CH2:4])[CH2:2][CH2:23]2)[CH:17]=[CH:16][CH:15]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

8

Reactant 4

HCID 7967CyclohexanoneHCID 8003PentaneHCID 3437981-Bromo-3-tert-butylbenzeneHCID 178418306HCID 178418306, compound

Product 1

HCID 597337431-(3-Tert-butyl-phenyl)-4-methylene-cyclohexanolYield 81%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 1.7 M tert-butyllithium in pentane (32.0 mL, 54.4 mmol) was added to a solution of 1-bromo-3-tert-butyl-benzene (5.54 g, 26.0 mmol) in tetrahydrofuran (60 mL) at −78° C. After stirring for 1 h, cyclohexanone (2.00 g, 18.2 mmol) in tetrahydrofuran (15 mL) was added. After stirring for 18 h, during which time the solution warmed to ambient temperature, the solution was diluted with saturated aqueous ammonium chloride and extracted with methylene chloride. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49:1, 24:1, 23:2 hexanes:ethyl acetate as the eluant to yield 3.61 g (81% yield) of 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexanol as a yellow oil.

Workup

  1. stirringAfter stirring for 18 h, during which time the solution
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed with 49:1, 24:1, 23:2 hexanes

Sources & evidence

ORD record
ord-f0668dfcdcd04782a255a587cf61429e
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Linked notes

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