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

HRID 2373053Notes

Reaction equation

HRID 2373053 reaction equation
B(O)(O)O.O[CH:6]([CH2:11][CH2:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1)[CH2:7][C:8](=[O:10])[CH3:9]>C1(C)C=CC=CC=1>[F:22][C:20]([F:21])([F:23])[C:17]1[CH:18]=[CH:19][C:14]([S:13][CH2:12][CH2:11][CH:6]=[CH:7][C:8](=[O:10])[CH3:9])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 7628Boric Acid2×HCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 95.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

0.85 Gram of boric acid was added to 80 ml of toluene, and the resulting mixture was refluxed for 3 hours with stirring. Thereafter, a solution of 6.00 g of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone in 20 ml of toluene was added dropwise thereto at the same refluxing temperature as the toluene solution of boric acid had been refluxed. And the mixture was further refluxed for 8 hours with stirring. The reaction mixture was washed three times with hot water and dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 5.40 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis =38.8 : 1) (purity: 99.4). The yield was 95.4%.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. temperatureAnd the mixture was further refluxed for 8 hours
  3. stirringwith stirring
  4. washThe reaction mixture was washed three times with hot water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoving the solvent from the mixture under reduced pressure

Sources & evidence

ORD record
ord-0d3b657ac8034dc9ac8d09fc7f54c50d
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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