p-Toluenesulfonic acid → 1-Phenylcyclohexene

HRID 2184392

Reaction equation

HRID 2184392 reaction equation
[C:1]1([C:7]2(O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]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:7]1([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 153191-Phenylcyclohexanol

Product 1

HCID 130431-Phenylcyclohexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-phenylcyclohexan-1-ol (24.9 mmol), p-toluenesulfonic acid (500 mg) and toluene (200 mL) are 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 is then allowed to cool to room temperature and concentrated under reduced vacuum. The crude material is then taken into methylene chloride, washed once with water, dried over potassium carbonate, filtered, and concentrated under reduced vacuum. This material can then be 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.

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. customThis material can then be purified via silica gel chromatography
  9. washeluting with a solvent of hexane/methylene chloride 9:1

Sources & evidence

ORD record
ord-9e5954cfd69347868396b871719b57fe
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Linked notes

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