p-Toluenesulfonic acid → HCID 57192219, compound

HRID 2249091Notes

Reaction equation

HRID 2249091 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8][CH:9]([CH3:17])[CH2:10][CH:11](O)[CH2:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([S:8][CH:9]([CH3:17])[CH2:10][CH:11]=[CH:12][C:13](=[O:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14883917HCID 14883917, compound

Product 1

HCID 57192219HCID 57192219, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.00 Gram of 6-(3-fluorophenylthio)-4-hydroxy- 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 0.96 g of 6-(3-fluorophenylthio)-3-hepten-2-one. (trans : cis =5.6 : 1) (purity: 89.3%). The yield was 92.5%.

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-0ccef9e20fba40779fb9fc3dab834d76
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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