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

HRID 1173175Notes

Reaction equation

HRID 1173175 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-5a1015c5a8e14142bdad1dbc26fa166f
Source dataset
uspto-grants-2010_11
Patent number
US07834021B2

Reaction notes

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