1-(3,5-Difluorophenyl)-4-pentylcyclohexan-1-OL → (4-Pentyl-1-cyclohexenyl)-3,5-difluorobenzene

HRID 566157Notes

Reaction equation

HRID 566157 reaction equation
O[C:2]1([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][CH2:3]1>C1(C)C=CC=CC=1>[CH2:8]([CH:5]1[CH2:6][CH2:7][C:2]([C:13]2[CH:14]=[C:15]([F:20])[CH:16]=[C:17]([F:19])[CH:18]=2)=[CH:3][CH2:4]1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

3

Reactant 1

HCID 212653251-(3,5-Difluorophenyl)-4-pentylcyclohexan-1-OL

Product 1

HCID 21265324(4-Pentyl-1-cyclohexenyl)-3,5-difluorobenzeneYield 56.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Mixture of (1-hydroxy-4-pentylcyclohexyl)-3,5-difluorobenzene (300 mmol), the Amberlist 15E (4.0 g), and 1,000 ml of toluene was refluxed for 6 hours. After allowed to cool, the Amberlist 15E was filtered off, the solvent was distilled off, and the residue was purified by column chromatography (eluent: heptane) to give a (4-pentyl-1-cyclohexenyl)-3,5-difluorobenzene (170 mmol).

Workup

  1. temperatureto cool
  2. filtrationthe Amberlist 15E was filtered off
  3. distillationthe solvent was distilled off
  4. customthe residue was purified by column chromatography (eluent: heptane)

Sources & evidence

ORD record
ord-80cb0e6b77364f528f14b33ed4662b8f
Source dataset
uspto-grants-2001_01
Patent number
US06174458B1

Reaction notes

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