Dimethyl Sulfoxide → 1-Ethenyl-4-(2-methylpropyl)benzene

HRID 1065535Notes

Reaction equation

HRID 1065535 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[CH3:12])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].CS(C)=O>O.[N+](C1C=CC=C([N+]([O-])=O)C=1)([O-])=O>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[CH2:12])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 1816541-[4-(2-Methylpropyl)phenyl]ethan-1-ol

Product 1

HCID 5761461-Ethenyl-4-(2-methylpropyl)benzeneYield 77.9%

Reagents, catalysts & solvents 2

HCID 74521,3-DinitrobenzeneCatalystHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To 6 g of α-(4-isobutylphenyl)ethyl alcohol were added 12 g of dimethyl sulfoxide and 0.1 g of m-dinitrobenzene as a polymerization inhibitor. The mixture was stirred at 160° C. for 8 hours. The resultant reaction liquor was cooled, diluted with water and then subjected to extraction with benzene. After the resulting organic layer was dried with magnesium sulfate, the solvent was distilled off. The residue thus obtained was distilled to give 4.2 g of 4-isobutylstyrene having the following physical properties.

Workup

  1. customThe resultant reaction liquor
  2. temperaturewas cooled
  3. extractionsubjected to extraction with benzene
  4. dry with materialAfter the resulting organic layer was dried with magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue thus obtained
  7. distillationwas distilled

Sources & evidence

ORD record
ord-4f7cd24f87a6423989f723a73b4ad459
Source dataset
uspto-grants-1982_05
Patent number
US04329507

Reaction notes

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