Potassium Carbonate → 2-Methyl-4-(2,5-dimethylphenyl)thio-2-butene

HRID 368932Notes

Reaction equation

HRID 368932 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:6])[CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[SH:21]>CC(C)=O>[CH3:5][C:4](=[CH:3][CH2:2][S:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[CH3:13])[CH3:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 776152,5-Xylenethiol

Product 1

HCID 129936832-Methyl-4-(2,5-dimethylphenyl)thio-2-buteneYield 100.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

80 ml of acetone, 9.1 g (0.06 mol) of 1-bromo-3-methyl-2-butene and 8.0 g (0.058 mol) of anhydrous potassium carbonate were added to 8.0 g (0.058 mol) of 2,5-dimethyl-thiophenol, and the mixture was refluxed under heat for 1 hour. After the completion of the reaction, a formed salt was removed by filtration, and the acetone was distilled off under reduced pressure. Then, ethyl acetate was added to the residue, and the mixture was washed with a saturated sodium chloride aqueous solution. The mixture was dried over anhydrous sodium sulfate, and then the ethyl acetate was distilled off to give 12 g (yield 100%) of 2-methyl-4-(2,5-dimethylphenyl)thio-2-butene.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 1 hour
  3. customAfter the completion of the reaction
  4. customa formed salt was removed by filtration
  5. distillationthe acetone was distilled off under reduced pressure
  6. additionThen, ethyl acetate was added to the residue
  7. washthe mixture was washed with a saturated sodium chloride aqueous solution
  8. dry with materialThe mixture was dried over anhydrous sodium sulfate
  9. distillationthe ethyl acetate was distilled off

Sources & evidence

ORD record
ord-09852a2aff6d4745afe727db2d477c94
Source dataset
uspto-grants-2000_10
Patent number
US06136755

Reaction notes

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