Water → 2-Methyl-7-(1-naphthyl)indene

HRID 1957717Notes

Reaction equation

HRID 1957717 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.O>C1(C)C=CC=CC=1>[CH3:5][C:4]1[CH2:11][C:1]2[C:6]([CH:3]=1)=[CH:5][CH:4]=[CH:3][C:2]=2[C:5]1[C:6]2[C:1](=[CH:11][CH:2]=[CH:1][CH:6]=2)[CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 962WaterHCID 6101p-Toluenesulfonic acid

Product 1

HCID 118072992-Methyl-7-(1-naphthyl)indeneYield 4,030.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The crude product was taken up in 200 cm3 of toluene, 0.5 g of p-toluene sulfonic acid was added, the reaction mixture was refluxed for 2 hours on a water separator and washed 3 times with 50 cm3 of saturated aqueous NaHCO3 solution, and the solvent was removed in vacuo. Filtration through 200 g of silica gel (hexane/methylene chloride) gave 10 g (86%) of 22 as a colorless oil.

Workup

  1. washwashed 3 times with 50 cm3 of saturated aqueous NaHCO3 solution
  2. customthe solvent was removed in vacuo
  3. filtrationFiltration through 200 g of silica gel (hexane/methylene chloride)

Sources & evidence

ORD record
ord-73a316471158465b9200e88d49ed8d1f
Source dataset
uspto-grants-1998_07
Patent number
US05786432

Reaction notes

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