Sodium Hydroxide → 2-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)cyclohex-2-en-1-one

HRID 35763

Reaktionsgleichung

Reaktionsgleichung von HRID 35763
Cl.[CH2:2]([O:4][NH2:5])[CH3:3].[OH-].[Na+].[OH:8][C:9]1[CH2:14][CH:13]([C:15]2[C:20]([CH3:21])=[C:19]([N+:22]([O-:24])=[O:23])[C:18]([CH3:25])=[C:17]([N+:26]([O-:28])=[O:27])[C:16]=2[CH3:29])[CH2:12][C:11](=[O:30])[C:10]=1[C:31](=O)[CH2:32][CH3:33]>C(O)C>[CH2:2]([O:4][N:5]=[C:31]([C:10]1[C:9](=[O:8])[CH2:14][CH:13]([C:15]2[C:16]([CH3:29])=[C:17]([N+:26]([O-:28])=[O:27])[C:18]([CH3:25])=[C:19]([N+:22]([O-:24])=[O:23])[C:20]=2[CH3:21])[CH2:12][C:11]=1[OH:30])[CH2:32][CH3:33])[CH3:3]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458871HCID 178458871, Verbindung

Produkt 1

HCID 1360051522-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)cyclohex-2-en-1-oneAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethoxyaminehydrochloride (0.36 g, 3.7 mmole) and then sodium hydroxide (0.15 g, 3.7 mmole) were added to a solution of 3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)-2-propionylcyclohex-2-en-1-one (1.0 g; 2.7 mmole) in absolute ethanol (80 ml). The mixture was stirred at room temperature for a period of 24 hours and then the ethanol was removed by evaporation under reduced pressure. The residue was treated with dichloromethane and the organic phase was washed twice with water and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the product recrystallized from ethanol to give 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)cyclohex-2-en-1-one (0.45 g; 39.8%) as a white solid, mp 170° C.

Aufarbeitung

  1. customthe ethanol was removed by evaporation under reduced pressure
  2. additionThe residue was treated with dichloromethane
  3. washthe organic phase was washed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by evaporation under reduced pressure
  6. customthe product recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-655cceb6fd76425f9e878a537420642d
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767879

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