p-Toluenesulfonic acid → 6-(trifluoromethyl)-1H-indene

HRID 2178769Notes

Reaction equation

HRID 2178769 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8](O)[CH2:7][CH2:6]2.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:4]=[C:5]2[C:9]([CH:8]=[CH:7][CH2:6]2)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 248204735-(trifluoromethyl)-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 190955106-(trifluoromethyl)-1H-indeneYield 96.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-(trifluoromethyl)indan-1-ol (1.6 g, 7.9 mmol) and p -toluenesulfonic acid (0.02 g, 0.1 mmol) in toluene (20 mL) was refluxed through a Dean-Stark trap for about 3 h. The solution was concentrated in vacuo and the residue was purified by flash chromatography on silica eluting with 5% EtOAc/hexane to afford the desired product as an oil (1.4 g, 96%).

Workup

  1. temperaturewas refluxed through a Dean-Stark trap for about 3 h
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by flash chromatography on silica eluting with 5% EtOAc/hexane

Sources & evidence

ORD record
ord-2cb533f7420d48feab4fa3031345e9b3
Source dataset
uspto-grants-2015_06
Patent number
US09067921B2

Reaction notes

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