p-Toluenesulfonic acid monohydrate → 2-Isopropyl-1H-indene

HRID 1953948Notes

Reaction equation

HRID 1953948 reaction equation
[CH:1]([CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]1O)([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH:1]([C:4]1[CH2:12][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 129273792-i-Propyl-1-indanol

Product 1

HCID 158656612-Isopropyl-1H-indene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-i-Propyl-1-indanol, non-purified, was dissolved in 300 ml of benzene to which was added 5 g of p-toluenesulfonic acid monohydrate and the resulting mixture was refluxed to allow dehydration reaction to occur. After the reaction was over, the reaction mixture was washed with saline, dried over magnesium sulfate, and concentrated in an evaporator. The reaction mixture was purified by column chromatography (silica gel, development solvent: n-hexane) to fractionate the target compound.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. customdehydration reaction
  3. washwas washed with saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in an evaporator
  6. customThe reaction mixture was purified by column chromatography (silica gel, development solvent: n-hexane)

Sources & evidence

ORD record
ord-fbc53dcc22d840bfbac39e4f6bc62e74
Source dataset
uspto-grants-2000_09
Patent number
US06121182

Reaction notes

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