Water → Cyclohexyl p-tolyl ketone

HRID 911604Notes

Reaction equation

HRID 911604 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[Cl-].[Cl-].[Al+3].O>C1(C)C=CC=CC=1>[CH:1]1([C:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 75938Cyclohexanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 76035Cyclohexyl p-tolyl ketoneYield 199.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve cyclohexanecarbonyl chloride (2 g, 13.6 mmol) in anhydrous toluene (30 mL). Cool the solution to 0° C., add aluminum trichloride (2.72 g, 20.46 mmol) in three portions and stir the reaction mixture at ambient temperature overnight Cool to 0° C., add slowly water and extract the mixture with EtOAc. Dry the organic layer over Na2SO4, filter and concentrate in vacuo. Purify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1) to give the desired intermediate (2.75 g, 100%).

Workup

  1. temperatureCool to 0° C.
  2. extractionextract the mixture with EtOAc
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the crude mixture by chromatography on silica gel eluting with hexane and hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-9cd5560f4ec64a3daff1d5004c316e8f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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