Cyclohexanone → 1-(3-Chlorophenyl)cyclohexanol

HRID 2177032Notes

Reaction equation

HRID 2177032 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][CH:7]=1.[C:10]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([OH:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 178478127HCID 178478127, compound

Product 1

HCID 2779261-(3-Chlorophenyl)cyclohexanolYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Chlorophenylmagnesium bromide (3.4 mL, 3.4 mmol) was added to a cooled (−10° C.) solution of cyclohexanone (0.3 g, 3.1 mmol) in anhydrous tetrahydrofuran slowly over 30 min. After complete addition, the reaction mixture was slowly warmed to room temperature, stirred for 18 hours. Again cooled (−5° C.), than quenched with sat. ammonium chloride solution over 30 min. The reaction mixture was extracted with ethyl acetate, dried, filtered and concentrated to afford 550 mg of 1-(3-chlorophenyl)cyclohexanol.

Workup

  1. additionAfter complete addition
  2. temperatureAgain cooled (−5° C.)
  3. customthan quenched with sat. ammonium chloride solution over 30 min
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-014140aa236f4741a929b5896d3ecd23
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

Loading…