Hydrochloric Acid → HCID 14534474, compound

HRID 2373033Notes

Reaction equation

HRID 2373033 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:20]=[C:21]([S:25][CH2:26][CH2:27][CH:28]=[O:29])[CH:22]=[CH:23][CH:24]=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:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:30])([F:17])[F:31])[CH:20]=1)[CH2:2][C:3](=[O:4])[CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 14517891HCID 14517891, compound

Product 1

HCID 14534474HCID 14534474, compoundYield 96.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

7.54 Grams of methyl acetoacetate were dissolved in 10 ml of water, and 9.07 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, 0.41 g of sodium acetate and 1.61 g of tetrabutylammonium bromide were added thereto and then 29.4 g of a toluene solution containing 33.8% of 3-(3-trifluoromethylphenylthio)propanal were added thereto. The mixture was stirred at 45°-50° C. for 6 hours. After the mixture had 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 14.92 g of crude 4-hydroxy-6-(3-trifluoromethylphenylthio)-2-hexanone (purity: 80.2%, yield: 96.7%).

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-fd7e596e76e44243859caf1c1d2cb67a
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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