p-Toluenesulfonic acid → 4-(cyclohex-1-en-1-yl)biphenyl

HRID 2184390Notes

Reaction equation

HRID 2184390 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3(O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:13]1([C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:12][CH:11]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22476583HCID 22476583, compound

Product 1

HCID 2273894-(cyclohex-1-en-1-yl)biphenylYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-Phenylphenyl)cyclohexan-1-ol (6.30 g, 24.9 mmol), p-toluenesulfonic acid (500 mg) and toluene (200 mL) were mixed together in a 500 mL 3 neck flask fitted with a thermometer and dean stark trap and stirred at reflux for 4 hours under a nitrogen atmosphere. The reaction was then let cool to room temperature and concentrated under reduced vacuum. The resulting semi-solid was taken into methylene chloride, washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum to yield 6.13 g as a solid. This material was purified via silica gel chromatography employing the Water's Prep 2000 and eluting with a solvent of hexane/methylene chloride 9:1 to yield the intermediate title compound (5.80 g, 99%) as a white solid. Fd M.S. 234.2 (M*).

Workup

  1. customfitted with a thermometer and dean stark trap
  2. temperatureat reflux for 4 hours under a nitrogen atmosphere
  3. concentrationconcentrated under reduced vacuum
  4. washwashed once with water
  5. dry with materialdried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced vacuum
  8. customto yield 6.13 g as a solid
  9. customThis material was purified via silica gel chromatography
  10. washeluting with a solvent of hexane/methylene chloride 9:1

Sources & evidence

ORD record
ord-13e02794a42442c3823d31422fc7674b
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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