3-Chloro-2-methyl-1-propene → 2-Methyl-3-(2,5-dimethylphenylthio)propane

HRID 974837Notes

Reaction equation

HRID 974837 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[SH:9].[CH2:10](Cl)[C:11](=[CH2:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:10][CH:11]([CH2:13][S:9][C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])[CH3:12]

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 776152,5-Xylenethiol

Product 1

HCID 234506662-Methyl-3-(2,5-dimethylphenylthio)propaneYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 100-ml eggplant type flask was charged with 6.9 g (50 mmol) of 2,5-dimethylthiophenol, 5.5 g (60 mmol, 1.2 equivalents) of methallyl chloride which was a halogenated olefin, 6.9 g (50 mmol, 1 equivalent) of potassium carbonate and 30 ml of acetone, and the mixture was refluxed under heat for 1 hour. The reaction mixture was allowed to cool, insolubles were removed by filtration, and the acetone was distilled off. The resultant residue was re-dispersed in n-hexane and washed with a saturated sodium chloride aqueous solution. An organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off to give 8.6 g (yield 89%) of 2-methyl-3-(2,5-dimethylphenylthio)propane.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 1 hour
  3. temperatureto cool
  4. custominsolubles were removed by filtration
  5. distillationthe acetone was distilled off
  6. additionThe resultant residue was re-dispersed in n-hexane
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-9b02db16191d424db3db831f1c6fa131
Source dataset
uspto-grants-1997_03
Patent number
US05607898

Reaction notes

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