2-Chlorocyclohexanone → 2-(4-Chlorophenyl)cyclohexan-1-one

HRID 1354089Notes

Reaction equation

HRID 1354089 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17]>CCOCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 178478191HCID 178478191, compound

Product 1

HCID 38395662-(4-Chlorophenyl)cyclohexan-1-oneYield 73.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-chlorophenylmagnesium bromide (200 mL of 1 M in ether, 200 mmol) was cooled in an ice-bath and a solution of 2-chlorocyclohexanone (26.5 g, 200 mmol) in 200 mL of ether was slowly added. The mixture was stirred at room temperature for 4 hours and was then concentrated under reduced pressure. Benzene (300 mL) was added and the mixture was heated under reflux for 12 h. Dilute aqueous HCl was added and the organic layer was separated, washed with brine, dried (sodium sulfate) and evaporated. Bulb-to-bulb distillation (2 mm) afforded 30.8 g of liquid product that subsequently crystallized.

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. additionBenzene (300 mL) was added
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 12 h
  5. additionDilute aqueous HCl was added
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (sodium sulfate)
  9. customevaporated
  10. distillationBulb-to-bulb distillation (2 mm)

Sources & evidence

ORD record
ord-a614873a65dd4c50b079bde0cf9bd5d0
Source dataset
uspto-grants-2007_05
Patent number
US07223767B2

Reaction notes

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