Cyclohexanone, 3,3-dimethyl- → HCID 68523959, compound

HRID 237758

Reaction equation

HRID 237758 reaction equation
[Mg].[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][C:18]1([CH3:25])[CH2:23][CH2:22][CH2:21][C:20](=[O:24])[CH2:19]1>BrC(Br)C.C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:20]2([OH:24])[CH2:21][CH2:22][CH2:23][C:18]([CH3:25])([CH3:17])[CH2:19]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 76322Cyclohexanone, 3,3-dimethyl-HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224Magnesium2×

Product 1

HCID 68523959HCID 68523959, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 112011,1-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

In a RB flask (250 mL) was placed magnesium turnings (2.08 g, 85.9 mmol), which were stirred under vacuum without solvent overnight. To the stirred magnesium turnings was added anhydrous THF (10 mL). To the resulting mixture at 50° C. was added several drops of dibromoethane, followed by 4-benzyloxybromobenzene (11.8 g, 42.9 mmol) in 40 ml of THF. After addition was complete, the reaction mixture was heated at 60° C. for 3 hours until a brownish-grey slurry was formed. The reaction mixture was cooled in an ice-bath and 3,3-dimethyl-cyclohexanone (3.87 g, 30.67 mmol) in THF (15 mL) was added dropwise. The reaction mixture was stirred at room temperature for one hour. The solvent was removed under reduced pressure. The residue was partitioned between EtOAc/aqueous NH4Cl. The aqueous phase was extracted three times with EtOAc. The organic phase was combined and dried (Na2SO4). Silica gel chromatography (EtOAc/heptane) provided 5.08 g of 1-(4-benzyloxy-phenyl)-3,3-dimethyl-cyclohexanol as a white solid.

Workup

  1. customIn a RB flask (250 mL) was placed
  2. additionAfter addition
  3. customwas formed
  4. temperatureThe reaction mixture was cooled in an ice-bath
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was partitioned between EtOAc/aqueous NH4Cl
  7. extractionThe aqueous phase was extracted three times with EtOAc
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-59ab291a648c42589a51c0ae76ef90c9
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Linked notes

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