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

Participants

Reaction Steps

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*).

Provenance & Evidence