Hydrochloric Acid → HCID 14534473, compound

HRID 2373035Notes

Reaction equation

HRID 2373035 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:34])([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29][CH2:30][CH2:31][CH:32]=[O:33])=[CH:25][CH:24]=1)[CH:19]([F:21])[F:20]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:33][CH:32]([CH2:31][CH2:30][S:29][C:26]1[CH:27]=[CH:28][C:23]([O:22][C:18]([F:17])([F:34])[CH:19]([F:21])[F:20])=[CH:24][CH:25]=1)[CH2:2][C:3](=[O:4])[CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 14347986HCID 14347986, compound

Product 1

HCID 14534473HCID 14534473, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

10.56 Grams of methyl acetoacetate were dissolved in 14 ml of water, and 13.9 g of a 28% 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, 0.6 g of sodium acetate and 2.3 g of tetrabutylammonium bromide were added thereto and then 43.4 g of a toluene solution containing 34.9% of 3-[4-(1,1,2,2-tetrafluoroethoxy)phenylthio]propanal were added thereto. The mixture was stirred at 45°-50° C. for 6 hours and then at room temperature for 12 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 21.88 g of crude 4-hydroxy-6-[4-(1,1,2,2-tetrafluoroethoxy)phenylthio]-2-hexanone (purity: 70.9%, yield: 83.9%).

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. waitat room temperature for 12 hours
  5. customthe organic layer was separated
  6. washwashed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customRemoving the solvent from the layer under reduced pressure

Sources & evidence

ORD record
ord-ab290f7cd3ea4064a89c7b8b1f08fff0
Source dataset
uspto-grants-1992_03
Patent number
US05101076

Reaction notes

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