p-Toluenesulfonic acid → HCID 57038213, compound

HRID 2373061Notes

Reaction equation

HRID 2373061 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[O:16][CH3:17])[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: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 14883921HCID 14883921, compound

Product 1

HCID 57038213HCID 57038213, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 4-hydroxy-6-(2-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 1 hour 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-(2-methoxyphenylthio)-3-hexen-2-one. (trans : cis =6.6 : 1) (purity: 91.9%). The yield was 94.6%.

Workup

  1. temperatureThe resulting mixture was refluxed for 1 hour
  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-5bb6a55a1708494fb097c564b7a07b5b
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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