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

HRID 2249086Notes

Reaction equation

HRID 2249086 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 AcidHCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

Product 1

HCID 572068326-(4-Trifluoromethylphenylthio)-3-hexen-2-oneYield 99.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
30 °C

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 and then cooled to 30° C. A solution of 6.00 g of 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone in 20 ml of toluene was added thereto, and the resulting mixture was further refluxed for 8 hours with stirring. The refluxed mixture was washed three times with hot water and then dried over anhydrous magnesium sulfate. Removing the solvent from the mixture under reduced pressure gave 5.58 g of 6-(4-trifluoromethylphenylthio)-3-hexen-2-one (trans : cis=38.7 : 1) (purity: 99.3%). The yield was 98.4%.

Workup

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. temperaturethe resulting mixture was further refluxed for 8 hours
  3. stirringwith stirring
  4. washThe refluxed 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-d95ba1d2598b461f8590fbfc6c24873b
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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