Chloranil → 4'-Pentyl-3,4,5-trifluorobiphenyl

HRID 1086766Notes

Reaction equation

HRID 1086766 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([F:20])[CH:13]=2)=[CH:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([F:20])[C:15]([F:19])=[C:16]([F:18])[CH:17]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 8371ChloranilHCID 151768401-(4-Pentylcyclohexen-1-yl)-3,4,5-trifluorobenzene

Product 1

HCID 151768434'-Pentyl-3,4,5-trifluorobiphenyl

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

1-(4-Pentylcyclohexen-1-yl)-3,4,5-trifluorobenzene as an intermediate obtained in Example 1 (5 g) was dissolved in xylene (50 ml), followed by adding chloranil (4.5 g), reacting the mixture under reflux for 10 hours, cooling the resulting material down to room temperature, filtering off the resulting deposited hydroquinone derivative, washing the filtrate with a dilute alkali aqueous solution, washing with water till the washing water became neutral, drying over anhydrous sodium sulfate, distilling off xylene from the organic layer, dissolving the residue in n-hexane, purifying the solution according to silica gel column chromatography, collecting fractions exhibiting a single spot according to thin layer chromatography, distilling off n-hexane and recrystallizing the residue from ethyl alcohol to obtain 4'-pentyl-3,4,5-trifluorobiphenyl (3.2 g).

Workup

  1. temperatureunder reflux for 10 hours
  2. filtrationfiltering off the resulting
  3. washwashing the filtrate with a dilute alkali aqueous solution
  4. washwashing with water till the washing water
  5. dry with materialdrying over anhydrous sodium sulfate
  6. distillationdistilling off xylene from the organic layer
  7. dissolutiondissolving the residue in n-hexane
  8. custompurifying the solution
  9. customcollecting fractions
  10. distillationdistilling off n-hexane
  11. customrecrystallizing the residue from ethyl alcohol

Sources & evidence

ORD record
ord-d7adb8ba6b934d86b4b799fd622c7acb
Source dataset
uspto-grants-1991_07
Patent number
US05032313

Reaction notes

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