Oxalic Acid → HCID 57001148, compound

HRID 2373041Notes

Reaction equation

HRID 2373041 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[C:16]([F:19])([F:18])[F:17])[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: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 971Oxalic AcidHCID 14678242HCID 14678242, compound

Product 1

HCID 57001148HCID 57001148, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

13.53 Grams of 4-hydroxy-6-(2-trifluoromethylphenylthio)-2-hexanone were dissolved in 150 ml of toluene, and 0.71 g of oxalic acid was added thereto. The resulting mixture was refluxed for 3.5 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 12.93 g of 6-(2-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis =4.4 : 1) (purity: 97.6%). The product was further column chromatographed to obtain a purified product having a refractive index (nD19) of 1.5263. The yield was 99.4%.

Workup

  1. temperatureThe resulting mixture was refluxed for 3.5 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-872fa4a5402d49709c1c1461470c6e18
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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