p-Toluenesulfonic acid → HCID 22476589, compound

HRID 2184391Notes

Reaction equation

HRID 2184391 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3(O)[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:11]=[CH:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 22476599HCID 22476599, compound

Product 1

HCID 22476589HCID 22476589, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(4-Phenylphenyl)cyclopentan-1-ol (7.50 g, 31.5 mmol), p-toluenesulfonic acid (650 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 allowed to 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 7.73 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 4:1 to yield the intermediate title compound (4.71 g, 68%) as a white solid. Fd M.S. 220.1 (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 7.73 g as a solid
  9. customThis material was purified via silica gel chromatography
  10. washeluting with a solvent of hexane/methylene chloride 4:1

Sources & evidence

ORD record
ord-11d3a9674e424da3bf0f174bca593372
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

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