Water → Indene

HRID 1066386Notes

Reaction equation

HRID 1066386 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.O.[C:13]1(C)C=CC=C[CH:14]=1>>[CH2:13]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:11]=[CH:14]1

Participants

4

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 7219IndeneYield 72%

Procedure

The crude product was taken up in 500 cm3 of toluene, 1.5 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 18.4 g (72%) of 29 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-426726c4590645a5ad16882bbf60fa96
Source dataset
uspto-grants-2001_06
Patent number
US06242544B1

Reaction notes

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