Hydrochloric Acid → 4-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanone

HRID 2249063Notes

Reaction equation

HRID 2249063 reaction equation
C(OC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Na+].Cl.C([O-])(=O)C.[Na+].[F:17][C:18]([F:31])([F:30])[C:19]1[CH:24]=[CH:23][C:22]([S:25][CH2:26][CH2:27][CH:28]=[O:29])=[CH:21][CH:20]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:29][CH:28]([CH2:27][CH2:26][S:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([F:30])([F:17])[F:31])=[CH:20][CH:21]=1)[CH2:2][C:3](=[O:4])[CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 143479823-(4-Trifluoromethylphenylthio)propanal

Product 1

HCID 145344724-Hydroxy-6-(4-trifluoromethylphenylthio)2-hexanoneYield 92%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.1 Grams of methyl acetoacetate were dissolved in 20 ml of water, and 18.2 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 35° C. or less. After having been stirred at 30°-35°C. for 3 hours, the mixture was adjusted to pH 7.5 with a concentrated aqueous hydrochloric acid solution. Thereafter, 0.82 g of sodium acetate and 3.22 g of tetrabutylammonium bromide were added thereto and then 54.85 g of a toluene solution containing 36.6% of 3-(4-trifluoromethylphenylthio)propanal were added thereto. The mixture was stirred at 45°-50° C. for 6 hours. After the mixture has been neutralized with a concentrated aqueous hydrochloric acid solution, the organic layer was separated, washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 27.08 g of crude 4-hydroxy-6-(4-trifluoromethylphenylthio)-2-hexanone (purity: 87.8 %, yield: 92.0%).

Workup

  1. temperatureby drops while cooling the mixture to 35° C. or less
  2. additionwere added
  3. stirringThe mixture was stirred at 45°-50° C. for 6 hours
  4. customthe organic layer was separated
  5. washwashed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customRemoving the solvent from the layer under reduced pressure

Sources & evidence

ORD record
ord-f5465ee5f4444f278fc3a32188e27f61
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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