p-Toluenesulfonic acid → HCID 57158943, compound

HRID 2249096Notes

Reaction equation

HRID 2249096 reaction equation
O[CH:2]([CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)[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][O:16][C:12]1[CH:11]=[C:10]([S:9][CH2:8][CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 19902764HCID 19902764, compound

Product 1

HCID 57158943HCID 57158943, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 4-hydroxy-6-(3-methoxyphenylthio)-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 0.96 g of 6-(3-methoxyphenylthio)-3-hexen-2-one. (trans : cis =4.2 : 1) (purity: 87.2%). The yield was 90.3%.

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-bcd52326d1ab4e13b4cf4f17df06c1be
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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