Water → 4-(Hydroxyimino)-4-phenylbutanoic acid

HRID 1059089

Reaktionsgleichung

Reaktionsgleichung von HRID 1059089
[C:1]([CH:9]([CH3:13])C(O)=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH:15][NH2:16].[C:17]([O-:20])(=[O:19])C.[Na+].O>CO>[OH:15][N:16]=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:13][C:17]([OH:20])=[O:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 103133562-Methyl-3-oxo-3-phenylpropanoic acid

Produkt 1

HCID 2319364-(Hydroxyimino)-4-phenylbutanoic acidAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
24.5 °C

Versuchsvorschrift

Benzoylpropionic acid (100 g) was suspended in methanol (300 ml) at room temperature, and hydroxyamine hydrochloride (46.8 g) and sodium acetate (138 g) were added. After stirring the mixture for 4.5 hr at room temperature at 22-27° C., pure water (500 ml) was added under cooling at 24-26° C. Seed crystal was added at 25° C., and the mixture was stirred at room temperature for about 1 hr, then cooled to 10° C. over about 30 min, and stirred at 5-10° C. for about 2 hr. The precipitated solid was collected by filtration, washed with pure water (100 ml×2) and dried under reduced pressure (40° C.) to give 4-(hydroxyimino)-4-phenylbutanoic acid (94.4 g) as a white solid in a yield of 87.1%.

Aufarbeitung

  1. temperatureunder cooling at 24-26° C
  2. additionSeed crystal was added at 25° C.
  3. stirringthe mixture was stirred at room temperature for about 1 hr
  4. temperaturecooled to 10° C. over about 30 min
  5. stirringstirred at 5-10° C. for about 2 hr
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with pure water (100 ml×2)
  8. customdried under reduced pressure (40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-c8d2efe5617449df83c19155b2572659
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518435B1

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