Cyclohexanone, 4,4-dimethyl- → HCID 68523971, compound

HRID 237735Notes

Reaction equation

HRID 237735 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][C:21](=[O:24])[CH2:20][CH2:19]1>C1COCC1>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:21]2([OH:24])[CH2:22][CH2:23][C:18]([CH3:25])([CH3:17])[CH2:19][CH2:20]2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 138166Cyclohexanone, 4,4-dimethyl-HCID 1388351-Bromo-4-phenylmethoxybenzeneHCID 5462224Magnesium

Product 1

HCID 68523971HCID 68523971, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

In a 250 mL round-bottomed flask was placed magnesium turnings (1.85 g, 76.1 mmol), which were stirred under vacuum without solvent overnight. To the turnings was added anhydrous THF (10 mL) and 4-benzyloxybromobenzene (10.0 g, 38.0 mmol) in anhydrous THF (40 ml) over 15 min. After the reaction was complete, the resulting gray slurry was stirred for 2 h at 60° C. To the slurry, cooled in an ice-water bath, was added 4,4-dimethyl-cyclohexanone (3.36 g, 26.6 mmol) in THF (15 mL). The reaction mixture was stirred for 1 hour at room temperature after which the solvent was removed under reduced pressure. The residue was partitioned between EtOAc/saturated NH4Cl. The mixture was extracted twice with EtOAc. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes) to give 4.14 g (50%) of 1-(4-benzyloxy-phenyl)-4,4-dimethylcyclohexanol.

Workup

  1. customIn a 250 mL round-bottomed flask was placed
  2. temperatureTo the slurry, cooled in an ice-water bath
  3. stirringThe reaction mixture was stirred for 1 hour at room temperature after which the solvent
  4. customwas removed under reduced pressure
  5. customThe residue was partitioned between EtOAc/saturated NH4Cl
  6. extractionThe mixture was extracted twice with EtOAc
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1a18eb60d1eb49b0acee45bc4b97a613
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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