p-Toluenesulfonic acid → 1H-Benz[e]indene

HRID 1585967Notes

Reaction equation

HRID 1585967 reaction equation
[CH:1]1(O)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]3=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 10103867HCID 10103867, compound

Product 1

HCID 117450041H-Benz[e]indeneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To the crude product of benzindanol dissolved in 200 ml of toluene was added 1.2 g (6.3 mmole) of p-toluenesulfonic acid, and the mixture was stirred at 80° C. for 15 minutes. The reaction was terminated with a saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with toluene, and the organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product of benzindene was obtained in an amount of 12.6 g, which was purified by column chromatography (Merck; solvent, hexane-ethyl acetate 0-1%). The product was obtained in an amount of 9.66 g (yield 85%).

Workup

  1. customThe reaction was terminated with a saturated aqueous sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with toluene
  3. washthe organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85f8bee3217143f796d2c5ba57e1b8c3
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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