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Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochloride → 2-[1-(3-Chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one

HRID 1906351
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1906351
Cl.[Cl:2][CH:3]=[CH:4][CH2:5][O:6][NH2:7].C([O-])(=O)C.[Na+].[OH:13][C:14]1[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([C:28](=[O:32])/[CH:29]=[CH:30]/[CH3:31])[C:21]=2[CH3:33])[CH2:17][C:16](=[O:34])[C:15]=1[C:35](=O)[CH2:36][CH3:37]>C(O)C>[Cl:2][CH:3]=[CH:4][CH2:5][O:6][N:7]=[C:35]([C:15]1[C:14](=[O:13])[CH2:19][CH:18]([C:20]2[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[C:22]([C:28](=[O:32])/[CH:29]=[CH:30]/[CH3:31])[C:21]=2[CH3:33])[CH2:17][C:16]=1[OH:34])[CH2:36][CH3:37]
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Komponenten

5

Edukt 3

HCID 158057Hydroxylamine, O-(3-chloro-2-propenyl)-, hydrochlorideHCID 517045Sodium AcetateHCID 178450140HCID 178450140, Verbindung

Produkt 1

HCID 1363321822-[1-(3-Chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-oneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

3-Chloroallyloxyamine hydrochloride (0.3 g) and then anhydrous sodium acetate (0.2 g) were added to a solution of 3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)-2-propionylcyclohex-2-en-1-one (0.7 g) in anhydrous ethanol (80 ml). The mixture was stirred briefly then allowed to stand at room temperature for 16 hours. The ethanol was removed by evaporation under reduced pressure using a rotary evaporator. The residue was treated with chloroform and the organic phase was washed twice with water (50 ml). The chloroform layer was dried over magnesium sulphate and the solvent was removed by evaporation under reduced pressure to give the product 2-[1-(3-chloroallyloxyimino)propyl]-3-hydroxy-5-(3-crotonyl-2,4,6-trimethylphenyl)cyclohex-2-en-1-one (0.7 g, 85%) as a colourless oil. Proton magnetic spectrum (CDCl3 ; δ in ppm); 1.19 (3H, t); 1.92 (3H, d, J=7 Hz); 2.09 (3H, s); 2.19 (3H, s); 2.39 (3H, s); 2.2-4.0 (7H, m); 4.4-4.8 (2H, m); 5.86.7 (4H, m); 6.86 (1H, s); 15.2 (1 H, bs).

Aufarbeitung

  1. customThe ethanol was removed by evaporation under reduced pressure
  2. customa rotary evaporator
  3. additionThe residue was treated with chloroform
  4. washthe organic phase was washed twice with water (50 ml)
  5. dry with materialThe chloroform layer was dried over magnesium sulphate
  6. customthe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4d235abf22ff4279bf3c3715ecec8224
Quelldatensatz
uspto-grants-1987_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04652303

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