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

HRID 974827Notes

Reaction equation

HRID 974827 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-dimethylthiophenol, 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 ethylacetate 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 ethylacetate was distilled off

Sources & evidence

ORD record
ord-1b929ff26abe44fb8a7cb974cf95e3fe
Source dataset
uspto-grants-1997_03
Patent number
US05607898

Reaction notes

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