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

HRID 2249080Notes

Reaction equation

HRID 2249080 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].S(=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 1118Sulfuric AcidHCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 57.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.46 Grams of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone were dissolved in 15 ml of toluene, and 0.35 g of concentrated aqueous sulfuric acid solution was added thereto. The resulting mixture was refluxed for 15 minutes with stirring, allowed to cool and then treated in the same manner as in Production example 34. Thus, 1.15 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis =4.2 : 1) were obtained (purity: 68.0%). The yield was 57.1%. Percent recovery of the starting material was 32.0%.

Workup

  1. temperatureThe resulting mixture was refluxed for 15 minutes
  2. temperatureto cool
  3. additiontreated in the same manner as in Production example 34

Sources & evidence

ORD record
ord-a16d9ece8b0c4cb2adc1c2956e519182
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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