p-Toluenesulfonic acid → HCID 57159538, compound

HRID 2249093Notes

Reaction equation

HRID 2249093 reaction equation
O[CH:2]([CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])[CH2:3][C:4](=[O:6])[CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[S:9][CH2:8][CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 148839194-Hydroxy-6-(2-methylphenylthio)-2-hexanone

Product 1

HCID 57159538HCID 57159538, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 4-hydroxy-6-(2-methylphenylthio)-2-hexanone 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 0.97 g of 6-(2-methylphenylthio)-3-hexen-2-one. (trans : cis =3.8 : 1) (purity: 94.7%). The yield was 99.8%.

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-7e471aa068064c9d882beac221896d28
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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