Hydrochloric Acid → HCID 14883921, compound

HRID 2249052Notes

Reaction equation

HRID 2249052 reaction equation
C(OC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Na+].Cl.C([O-])(=O)C.[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25][CH2:26][CH2:27][CH:28]=[O:29]>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:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH3:17])[CH2:2][C:3](=[O:4])[CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 19902766HCID 19902766, compound

Product 1

HCID 14883921HCID 14883921, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4.93 Grams of methyl acetoacetate were dissolved in 7.5 ml of water, and 6.34 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, 0.30 g of sodium acetate and 1.00 g of tetrabutylammonium bromide were added thereto and then an additional hydrochloric acid was added thereto so that the mixture had a pH of 6.9. Further, 17.8 g of a toluene solution containing 27.5% of 3-(2-methoxyphenylthio)propanal were added thereto and the resulting mixture was stirred at 45°-50° C. for 9 hours. The organic layer was separated from the mixture. It 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 5.78 g of crude 4-hydroxy-6-(2-methoxyphenylthio)-2-hexanone (purity: 79.9%, yield: 75.7%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5705.

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 was separated from the mixture
  5. washIt was 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-8a140d733caa4a469f420b586ce6617d
Source dataset
uspto-grants-1991_08
Patent number
US05041679

Reaction notes

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