p-Toluenesulfonic acid → HCID 57285551, compound

HRID 2373063Notes

Reaction equation

HRID 2373063 reaction equation
O[CH:2]([CH2:7][CH:8]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[CH3:9])[CH2:3][C:4](=[O:6])[CH3:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([S:10][CH:8]([CH3:9])[CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5])[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14883922HCID 14883922, compound

Product 1

HCID 57285551HCID 57285551, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 4-hydroxy-6-(3-methoxyphenylthio)-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 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 1.05 g of 6-(3-methoxyphenylthio)-3-hepten-2-one. (trans : cis =4.8 : 1) (purity: 82.7%). The yield was 93.5%.

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-78ce3b6a5e6843bf98557a82d875ba99
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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