Sodium Hydroxide → Desoxyanisoin Oxime

HRID 2286276

Reaktionsgleichung

Reaktionsgleichung von HRID 2286276
[C:1]1([C:9]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)=O)[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1.Cl.[NH2:21][OH:22].[OH-].[Na+]>CO.O>[C:1]1([C:9](=[N:21][OH:22])[CH2:11][C:12]2[CH:19]=[CH:18][C:15]([O:16][CH3:17])=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:4]([O:5][CH3:6])=[CH:3][CH:2]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 67120DesoxyanisoinHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 231097Desoxyanisoin OximeAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Desoxyanisoin (98%, 52.2 g., 0.2 mole) and hydroxylamine hydrochloride (15.3 g., 0.22 mole) are slurried in a mixture of methanol (300 ml) and water (200 ml) and sodium hydroxide (16 g., 0.4 mole) is added slowly. The mixture is stirred for 15 minutes, then placed in a hot water bath (70° C.) and stirred an additional hour. Methanol is then added to the hot mixture until solution is almost complete, the mixture is filtered and concentrated to remove most of the methanol, then cooled with the addition of ice-water. Filtered, dissolved the resulting solid in ethyl acetate, extracted with brine. Dried the organic layer (Na2SO4), filtered and concentrated to obtain 53.5 g (98.5%) of the oxime as a yellow solid.

Aufarbeitung

  1. additionis added slowly
  2. customplaced in a hot water bath
  3. stirring(70° C.) and stirred an additional hour
  4. filtrationthe mixture is filtered
  5. concentrationconcentrated
  6. customto remove most of the methanol
  7. temperaturecooled with the addition of ice-water
  8. filtrationFiltered
  9. dissolutiondissolved the resulting solid in ethyl acetate
  10. extractionextracted with brine
  11. dry with materialDried the organic layer (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ebe1373d01a44967b359eaa67873688b
Quelldatensatz
uspto-grants-1982_04
Patentnummer
US04327222

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