p-Toluenesulfonic acid → 2,3-Dihydro-1H-indene-4-carbonitrile

HRID 1646608Notes

Reaction equation

HRID 1646608 reaction equation
O[CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]#[N:12])[C:5]=2[CH2:4][CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCCl>[CH2:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[C:11]#[N:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 145153071-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile

Product 1

HCID 155761132,3-Dihydro-1H-indene-4-carbonitrileYield 46.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

5.9 g of 1-hydroxy-4-indanecarbonitrile in 60 ml of 1,2,-dichloroethane and 210 mg of paratoluene sulphonic acid (APTS, 1H2O) are taken to reflux for 2 hours. After cooling to ambient temperature and concentrating to dryness at 40° C. under reduced pressure, the residue is chromatographed on silica in a hexane-isopropyl ether mixture (9-1), and 2.46 g of expected product is isolated.

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationconcentrating to dryness at 40° C. under reduced pressure
  3. customthe residue is chromatographed on silica in a hexane-isopropyl ether mixture (9-1)

Sources & evidence

ORD record
ord-cb67a38d0e1c481d93f4081a4c4abb94
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

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