Methyl vinyl ketone → 4,4-Bis(4-fluorophenyl)cyclohex-2-enone

HRID 1243849Notes

Reaction equation

HRID 1243849 reaction equation
[CH:1]([C:3]([CH3:5])=[O:4])=[CH2:2].[OH-].[K+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:16]=O)=[CH:11][CH:10]=1>C(O)C.C(OCC)C>[F:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:16][CH2:5][C:3](=[O:4])[CH:1]=[CH:2]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 14797Potassium HydroxideHCID 125491042,2-Bis(4-fluorophenyl)acetaldehyde

Product 1

HCID 219287994,4-Bis(4-fluorophenyl)cyclohex-2-enone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

1.7 cm3 of methyl vinyl ketone and 0.39 g of potassium hydroxide pellets dissolved in 3 cm3 of ethanol are successively added to a solution, cooled to 0° C., of 4 g of bis(4-fluorophenyl)acetaldehyde in 35 cm3 of ethyl ether. The temperature is left in the region of 20° C. for 24 hours. The mixture is concentrated to dryness under reduced pressure, 75 cm3 of dichloromethane are added and the mixture is washed with twice 75 cm3 of distilled water. After drying over magnesium sulphate and concentrating to dryness under reduced pressure, the residue is purified by flash chromatography on silica gel (30–70 μm), eluting with pure dichloromethane; 3 g of 4,4-bis(4-fluorophenyl)cyclohex-2-enone are thus obtained in the form of a pale yellow oil, the characteristics of which are as follows:

Workup

  1. additionare successively added to a solution
  2. concentrationThe mixture is concentrated to dryness under reduced pressure, 75 cm3 of dichloromethane
  3. additionare added
  4. washthe mixture is washed with twice 75 cm3 of distilled water
  5. dry with materialAfter drying over magnesium sulphate
  6. concentrationconcentrating to dryness under reduced pressure
  7. customthe residue is purified by flash chromatography on silica gel (30–70 μm)
  8. washeluting with pure dichloromethane

Sources & evidence

ORD record
ord-66f69b3d98b6436596ad5dfac3be7194
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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