p-Toluenesulfonic acid → HCID 22252737, compound

HRID 897071Notes

Reaction equation

HRID 897071 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:9][CH:10]=[C:11]([CH3:13])[CH3:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:12][C:11]1([CH3:13])[C:4]2[C:3](=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[S:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 106348752-Bromo-1-(3-methylbut-2-enylthio)benzene

Product 1

HCID 22252737HCID 22252737, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

26.00 g (102.0 mmol) of 2-bromo-1-(3-methylbut-2-enylthio)benzene, 180 ml of toluene and 23.20 g (122.0 mmol) of para-toluenesulphonic acid are introduced into a three-necked flask. The reaction medium is refluxed for four hours and is then evaporated to dryness. The residue is taken up in aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate, and the organic phase is separated out after settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica and eluted with heptane. 20 g (76%) of the expected compound are collected in the form of an orange-coloured oil.

Workup

  1. temperatureThe reaction medium is refluxed for four hours
  2. customis then evaporated to dryness
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is separated out
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with heptane
  10. custom20 g (76%) of the expected compound are collected in the form of an orange-coloured oil

Sources & evidence

ORD record
ord-89f26375daa94ebbba35d32459cff721
Source dataset
uspto-grants-2005_07
Patent number
US06921777B2

Reaction notes

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