Hydrochloric Acid → HCID 14883919, Verbindung

HRID 2373018

Reaktionsgleichung

Reaktionsgleichung von HRID 2373018
C(OC)(=O)[CH2:2][C:3]([CH3:5])=[O:4].[OH-].[Na+].Cl.C([O-])(=O)CC(C)C.[Na+].[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27][CH2:28][CH2:29][CH:30]=[O:31]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[OH:31][CH:30]([CH2:29][CH2:28][S:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH3:20])[CH2:2][C:3](=[O:4])[CH3:5]

Komponenten

9

Edukt 5

HCID 313Hydrochloric Acid2×HCID 7757Methyl acetoacetateHCID 14798Sodium HydroxideHCID 145034523-[(2-Methylphenyl)sulfanyl]propanalHCID 23673832Sodium Isovalerate

Produkt 1

HCID 14883919HCID 14883919, VerbindungAusbeute 62,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

9.86 Grams of methyl acetoacetate were dissolved in 15 ml of water, and 12.67 g of a 30% aqueous sodium hydroxide solution was 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, 1.07 g of sodium isovalerate and 2.42 g of tetrabutylammonium bromide were added thereto. Then a concentrated aqueous hydrochloric acid solution was added to the mixture so that the mixture had a pH of 6.8. Further, 26.2 g of a toluene solution containing 32.7% of 3-(2-methylphenylthio)propanal was added thereto and 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. Thereafter the layer was dried over anhydrous magnesium sulfate. Removing the solvent from the layer under reduced pressure gave 10.32 g of crude 4-hydroxy-6-(2-methylphenylthio)-2-hexanone (purity: 67.8%, yield: 62.1%). A purified product was obtained by column chromatography. The purified product had an nD21 of 1.5660.

Aufarbeitung

  1. temperatureby drops while cooling the mixture to 25° C. or less
  2. additionwas added
  3. stirringstirred 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 materialThereafter the layer was dried over anhydrous magnesium sulfate
  7. customRemoving the solvent from the layer under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a8fe1d0bbd50495985356537ebea3c14
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05101076

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