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

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Reaction Steps

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%.

Provenance & Evidence