Cyclohexanone → 1-(3-Methoxyphenyl)cyclohexan-1-ol

HRID 852629Notes

Reaction equation

HRID 852629 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CCOCC.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([OH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 7967CyclohexanoneHCID 178490745HCID 178490745, compound

Product 1

HCID 146851021-(3-Methoxyphenyl)cyclohexan-1-olYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 3-methoxyphenylmagnesium bromide (1M in THF, 61 ml, 61 mmol, 1 equiv) at 0° C. was slowly added cyclohexanone (6 g, 61 mmol, 1 equiv) in Et2O (30 ml). The resulting mixture was stirred at room temperature for 4 h then poured in H2O at 0° C. The two layers were separated and the aqueous phase was extracted three times with Et2O. The combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo to give 1-[3-(methyloxy)phenyl]cyclohexanol (D314) (12.4 g, 100%) as a pale yellow oil which was used in the next step without further purification.

Workup

  1. customat 0° C.
  2. customThe two layers were separated
  3. extractionthe aqueous phase was extracted three times with Et2O
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bec0111f2a74284a85df968fbc9f0dc
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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