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

HRID 35762

Reaktionsgleichung

Reaktionsgleichung von HRID 35762
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])=[CH:19][C:18]([CH3:22])=[C:17]([N+:23]([O-:25])=[O:24])[C:16]=2[CH3:26])[CH2:12][C:11](=[O:27])[C:10]=1[C:28](=O)[CH2:29][CH3:30]>C(O)C>[CH2:2]([O:4][N:5]=[C:28]([C:10]1[C:11](=[O:27])[CH2:12][CH:13]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[C:17]([N+:23]([O-:25])=[O:24])[C:16]=2[CH3:26])[CH2:14][C:9]=1[OH:8])[CH2:29][CH3:30])[CH3:3]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 76850O-ethylhydroxylamine hydrochlorideHCID 178458845HCID 178458845, Verbindung

Produkt 1

HCID 1362095012-[1-(Ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)cyclohex-2-en-1-oneAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethoxyamine hydrochloride (0.26 g; 2.7 mmole) and then sodium hydroxide (0.11 g; 2.7 mmole) were added to a solution of 3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)-2-propionylcyclohex-2-en-1-one (0.6 g; 1.8 mmole) in absolute ethanol (150 ml). The mixture was stirred at room temperature for a period of 18 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 dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give the product, 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-nitrophenyl)cyclohex-2-en-1one (0.56 g; 83.2%) as a pale yellow oil. The product was characterized by proton nuclear magnetic resonance spectroscopy and the spectroscopic data is recorded in Table 5, Example 37.

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

Quellen und Nachweise

ORD-Eintrag
ord-ea4ac235a9be4f3da8afc55c10b4281d
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767879

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