2',4'-Dihydroxyacetophenone → 2',4'-Dihydroxyacetophenone oxime

HRID 706246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706246
[CH3:1][C:2]([C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[CH:8][C:9]=1[OH:10])=O.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>O.O1CCOCC1>[OH:10][C:9]1[CH:8]=[C:7]([OH:11])[CH:6]=[CH:5][C:4]=1[C:2](=[N:13][OH:14])[CH3:1]

Komponenten

5

Edukt 3

HCID 69902',4'-DihydroxyacetophenoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Produkt 1

HCID 3451682',4'-Dihydroxyacetophenone oximeAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of 2,4-dihydroxyacetophenone (25 g, 0.16 mol), hydroxylamine hydrochloride (14.8 g, 0.21 mol), sodium acetate (20 g, 0.24 mol) and water/dioxane (300 mL, 1:1) was stirred at room temperature for three days before the mixture was partitioned between chloroform and water. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (11.67 g): 1H NMR (CD3OD, 200 MHz): δ=7.26 (m, 1H), 6.28 (m, 2H), 4.88 (s, 2H), 3.29 (m, 1H), 2.24 (s, 3H).

Aufarbeitung

  1. customwas partitioned between chloroform and water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-8528ec2175234dc682ae2ddfdca42a15
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174976B2

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