2-Methylbenzenesulfonic acid → 1-(3-Bromopropyl)-4-ethenylbenzene

HRID 1170770Notes

Reaction equation

HRID 1170770 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1C(C)O.[C:14]1(C)C(S(O)(=O)=O)=CC=C[CH:19]=1>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:14]=[CH2:19])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 69252-Methylbenzenesulfonic acidHCID 867612063-bromopropyl-a-Methylbenzenemethanol2×

Product 1

HCID 184688641-(3-Bromopropyl)-4-ethenylbenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The product from Example 2 is used as a stating material in this procedure. The resulting product from Example 2 was diluted in 200 mL of toluene. Next, 0.125 g of toluensulfonic acid was added to the reaction mixture. The reaction mixture was refluxed under argon atmosphere for 44 hours. The mixture was then washed with 50 mL of water and the solvent was removed under vacuum. The resulting product was then purified by silica gel chromatography with the use of 90% hexane and 10% ethyl acetate. The resulting product was recovered as the solvent was removed under vacuum.

Workup

  1. temperatureThe reaction mixture was refluxed under argon atmosphere for 44 hours
  2. washThe mixture was then washed with 50 mL of water
  3. customthe solvent was removed under vacuum
  4. customThe resulting product was then purified by silica gel chromatography with the use of 90% hexane and 10% ethyl acetate
  5. customThe resulting product was recovered as the solvent
  6. customwas removed under vacuum

Sources & evidence

ORD record
ord-7cf7ba6071274ae8a936f87741eae82a
Source dataset
uspto-grants-2010_11
Patent number
US07829155B1

Reaction notes

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