Cyclohexanecarbonyl chloride → 1-Cyclohexyl-2-phenylethanone

HRID 1789992Notes

Reaction equation

HRID 1789992 reaction equation
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH:10]1([C:16]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 178419772HCID 178419772, compound

Product 1

HCID 27946121-Cyclohexyl-2-phenylethanoneYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 11 ml of 0.5 M solution of benzyl zinc bromide in anhydrous tetrahydrofuran were added at 0° C. 5 mg of bis-triphenylphospinepalladium dichloride and 0.66 ml of cyclohexanecarbonyl chloride. The mixture was stirred at r.t. for 1.5 h, quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate. The collected organic layers were washed with water, dried (Na2SO4) and the solvent was evaporated under vacuum. The crude was purified by flash chromatography eluting with petroleum ether-EtOAc 95:5 to give 0.78 g (52%) of the title compound.

Workup

  1. customquenched with a saturated solution of ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe collected organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was evaporated under vacuum
  6. customThe crude was purified by flash chromatography
  7. washeluting with petroleum ether-EtOAc 95:5

Sources & evidence

ORD record
ord-77ac6db584834c1f8375001625f5f875
Source dataset
uspto-grants-2006_07
Patent number
US07071197B2

Reaction notes

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