1,4-Cyclohexanedione → 4-Hydroxy-4-phenylcyclohexan-1-one

HRID 1025673Notes

Reaction equation

HRID 1025673 reaction equation
[C:1]1(=[O:8])[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[C:9]1([Mg]Br)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[OH:7][C:4]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:1](=[O:8])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 125111,4-CyclohexanedioneHCID 178418255HCID 178418255, compound

Product 1

HCID 5837414-Hydroxy-4-phenylcyclohexan-1-oneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1,4-cyclohexanedione (6.72 g, 60 mmol) in THF (100 mL) cooled in an ice bath was added a 1 M solution of phenyl magnesium bromide in THF (20 mL, 20 mmol). The mixture was stirred at room temperature for 3 hours and quenched with an NH4Cl solution. The resulting solution was extracted with EtOAc three times. The combined organic phase was washed with brine, dried over MgSO4 and concentrated. Purification on silica gel eluting with 1:1 EtOAc/hexanes yielded 0.83 g (22%) of the title compound. MS calculated (M+H)+ 190, found 173 (M+H−H2O)+.

Workup

  1. customquenched with an NH4Cl solution
  2. extractionThe resulting solution was extracted with EtOAc three times
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customPurification on silica gel eluting with 1:1 EtOAc/hexanes

Sources & evidence

ORD record
ord-295d02f4713944859f24eb521018976c
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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