p-Toluenesulfonic acid → HCID 57100617, compound

HRID 2249094Notes

Reaction equation

HRID 2249094 reaction equation
O[CH:2]([CH2:7][CH:8]([S:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1)C)[CH2:3][C:4](=[O:6])[CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([S:10][CH2:8][CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14692816HCID 14692816, compound

Product 1

HCID 57100617HCID 57100617, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 4-hydroxy-6-(4-methylphenylthio)-2-heptanone was dissolved in 100 ml of toluene, and 0.02 g of p-toluene sulfonic acid was added thereto. The resulting mixture was refluxed for 2.5 hours with stirring. After having been cooled, the mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and then saturated aqueous sodium chloride solution. Then the mixture was dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 0.74 g of 6-(4-methylphenylthio)-3-hexen-2-one. (trans : cis =5.5 : 1) (purity: 83.5%). The yield was 66.7%.

Workup

  1. temperatureThe resulting mixture was refluxed for 2.5 hours
  2. temperatureAfter having been cooled
  3. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThen the mixture was dried over anhydrous magnesium sulfate
  5. customRemoving the solvent from the mixture under reduced pressure

Sources & evidence

ORD record
ord-419b57e11b95432eb9a6c205d4f7d897
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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