Hydrochloric Acid → HCID 14883917, compound

HRID 2249055Notes

Reaction equation

HRID 2249055 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]1[CH:19]=[C:20]([S:24][CH:25]([CH3:29])[CH2:26][CH:27]=[O:28])[CH:21]=[CH:22][CH:23]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[F:17][C:18]1[CH:19]=[C:20]([S:24][CH:25]([CH3:29])[CH2:26][CH:27]([OH:28])[CH2:2][C:3](=[O:4])[CH3:5])[CH:21]=[CH:22][CH:23]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 19902770HCID 19902770, compound

Product 1

HCID 14883917HCID 14883917, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

9.86 Grams of methyl acetoacetate were dissolved in 15 ml of water, and 12.67 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, 0.62 g of sodium acetate and 2.42 g of tetrabutylammonium bromide were added thereto and then an additional concentrated aqueous hydrochloric acid solution was added thereto so that the mixture had a pH of 6.9. Further, 27.4 g of a toluene solution containing 36.6% of 3-(3-fluorophenylthio)butanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer separated from the mixture was washed with a 5% aqueous acetic acid solution and then with a saturated aqueous sodium chloride solution. Then it was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 12.49 g of crude-6-(3-fluorophenylthio)-4-hydroxy-2-heptanone (purity: 90.8%, yield: 87.4%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5342.

Workup

  1. temperatureby drops while cooling the mixture to 25° C. or less
  2. additionwere added
  3. stirringthe resulting mixture was stirred at 45°-50° C. for 9 hours
  4. customThe organic layer separated from the mixture
  5. washwas washed with a 5% aqueous acetic acid solution
  6. dry with materialThen it was dried over anhydrous magnesium sulfate
  7. customRemoving the solvent from the layer under reduced pressure

Sources & evidence

ORD record
ord-78a740e2fb4a4c7ea09a87a77404dc2c
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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