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

HRID 2249073Notes

Reaction equation

HRID 2249073 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].C(O)(=O)C(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 971Oxalic AcidHCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20.75 Grams of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone were dissolved in 100 ml of toluene, and 1.00 g of oxalic acid was added thereto. The resulting mixture was refluxed for 1.25 hours 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 17.13 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis =3.7 : 1) (purity: 97.8%). The product was further column chromatographed to obtain a purified product having a refractive index (nD20) of 1.5274. The yield was 86.0%.

Workup

  1. temperatureThe resulting mixture was refluxed for 1.25 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-4878813e2cc4480c9c035375b7cdf706
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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