Phosphoric Acid → 6-(4-Trifluoromethylphenylthio)-3-hexen-2-one

HRID 2249087Notes

Reaction equation

HRID 2249087 reaction equation
O[CH:2]([CH2:7][CH2:8][S:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[CH2:3][C:4](=[O:6])[CH3:5].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[F:18][C:16]([F:17])([F:19])[C:13]1[CH:14]=[CH:15][C:10]([S:9][CH2:8][CH2:7][CH:2]=[CH:3][C:4](=[O:6])[CH3:5])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 84.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.00 Grams of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone were dissolved in 50 ml to toluene, and 0.50 g of 85% phosphoric 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 with a saturated aqueous sodium chloride solution. Then the mixture was dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 2.83 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis=28 : 1) (purity: 84.2%). The yield was 84.7%.

Workup

  1. additionwas added
  2. temperatureThe resulting mixture was refluxed for 1 hour
  3. temperatureAfter having been cooled
  4. washthe mixture was washed with a saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialThen the mixture was dried over anhydrous magnesium sulfate
  6. customRemoving the solvent from the mixture under reduced pressure

Sources & evidence

ORD record
ord-7830c6500da34c979abcaa33661a7b05
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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