Hydroxyamine hydrochloride → (p-Chlorophenyl)-1,1,1-trifluoro-2-propanone oxime

HRID 1030783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030783
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].C([O-])(=O)C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[N:16][OH:17])[C:10]([F:13])([F:12])[F:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 151139833-(4-Chlorophenyl)-1,1,1-trifluoropropan-2-one

Produkt 1

HCID 85405208(p-Chlorophenyl)-1,1,1-trifluoro-2-propanone oximeAusbeute 110,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel3×

Versuchsvorschrift

A solution of 3-(p-chlorophenyl)-1,1,1-trifluoro-2-propanone (10.0 g, 0.045 mol) in ethanol (60 mL) is treated with a solution of hydroxylamine hydrochloride (4.68 g, 0.067 mol) in water (20 mL) and then with a solution of sodium acetate (5.53 g, 0.067 mol) in water (20 mL). The reaction mixture is refluxed for 2 hours, cooled, diluted with water, and extracted with ether. The combined ether extracts are washed sequentially with water and brine, dried (Na2SO4) and evaporated to a liquid which solidifies upon standing to give the title compound as white needles (11.84 g): IR (neat) 3300 cm-1 (broad); 1H NMR (CDCl3) δ3.86 (s, 2H, CH2), 7.23 and 7.30 (AB,JAB =8.6 Hz, ArH), 19F NMR δ-69.2; 13C NMR δ29.3 (s, CH2), 120.8 (q, 1JCF =274.5 Hz, CF3), 128.8, 130.3, 132.5, 133.1 (Aromatic C), 148.4 (q 2JCF =32.1 Hz, CO).

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether
  4. washThe combined ether extracts are washed sequentially with water and brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to a liquid which

Quellen und Nachweise

ORD-Eintrag
ord-6ec3b190509848da805de077e336d47c
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106985

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