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

HRID 2249085Notes

Reaction equation

HRID 2249085 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].B(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 7628Boric AcidHCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 98.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.00 Grams of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone were dissolved in 50 ml of toluene, and 0.30 g of boric acid was added thereto. The resulting mixture was refluxed for 8 hours with stirring. The refluxed mixture, after allowed to cool, 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 2.85 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis =28.6 : 1)(purity: 97.7%). The yield was 98.7%.

Workup

  1. temperatureThe resulting mixture was refluxed for 8 hours
  2. temperatureto cool
  3. washwas 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-8e054dc008a64cbfacc98e8fc37640c9
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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