Hydrochloric Acid → HCID 14883916, compound

HRID 2249058Notes

Reaction equation

HRID 2249058 reaction equation
C(OC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Na+].Cl.C([O-])(=O)C.[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][CH2:25][CH2:26][CH:27]=[O:28])=[CH:20][CH:19]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([S:24][CH2:25][CH2:26][CH:27]([OH:28])[CH2:2][C:3](=[O:4])[CH3:5])=[CH:22][CH:23]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 14503453HCID 14503453, compound

Product 1

HCID 14883916HCID 14883916, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

15.10 Grams of methyl acetoacetate were dissolved in 20 ml of water, and 18.20 g of a 30% aqueous sodium hydroxide solution were added thereto by drops while cooling the mixture to 25° C. or less. After having been stirred at 30°-35° C. for 3 hours, the mixture was adjusted to pH 7.0 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 an additional concentrated aqueous hydrochloric acid solution was added to the mixture so that the mixture was adjusted to pH 6.9. Further, 54.45 g of a toluene solution containing 36.8% of 3-(4-chlorophenylthio)propanal were added thereto and was stirred at 45°-50° C. for 6 hours. The organic layer separated from the layer was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then the layer was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 27.08 g of crude 6-(4-chloro-phenylthio)-4-hydroxy-2-hexanone (purity: 87.83%, yield: 92.0%).

Workup

  1. temperatureby drops while cooling the mixture to 25° C. or less
  2. additionwere added
  3. stirringwas stirred at 45°-50° C. for 6 hours
  4. customThe organic layer separated from the layer
  5. washwas washed with a 5% aqueous acetic acid solution
  6. dry with materialThen the layer was dried over anhydrous magnesium sulfate
  7. customRemoving the solvent from the layer under reduced pressure

Sources & evidence

ORD record
ord-15fe2823071a4d77a386ffc9c0a07d95
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

Loading…