Acetic Acid → 1,1,1-Trifluoro-3-(hydroxyimino)-5-(2-methylphenyl)pentan-2-one

HRID 647369

Reaktionsgleichung

Reaktionsgleichung von HRID 647369
[N:1]([O-:3])=O.[K+].[F:5][C:6]([F:20])([F:19])[C:7](=[O:18])[CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17].C(O)(C)(C)C.C(O)(=O)C>O>[F:5][C:6]([F:19])([F:20])[C:7](=[O:18])[C:8](=[N:1][OH:3])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6386tert-ButanolHCID 516910Potassium nitrite2×HCID 155687561,1,1-Trifluoro-5-(2-methylphenyl)pentan-2-one

Produkt 1

HCID 714141471,1,1-Trifluoro-3-(hydroxyimino)-5-(2-methylphenyl)pentan-2-oneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel3×

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of potassium nitrite (22.2 g, 0.26 mol) in water (total volume=7.4 mL) was added in one portion to a stirred solution of 1,1,1-trifluoro-5-(2-methylphenyl)-2-pentanone (20 g, 0.087 mol), tert-butanol (25 mL) and acetic acid (25 mL) at 25° C. The reaction mixture was stirred at 25° C. for 2.5 hr. Another solution of potassium nitrite (7.5 g, 0.088 mol) in water (2.5 mL) then was added. After stirring for 1.5 hr, the reaction mixture was poured into water. The resulting mixtutre was extracted with diethyl ether (3x). The combined ether extracts were washed with water and then washed with a saturated aqueous solution of NaHCO3. Thereafter, the organic extract was dried (MgSO4) and concentrated under reduced pressure to give the title compound (22.1 g, 98% yield) as a yellow crystalline mass. This product was used for the reaction described in the following example. A sample of the product, recrystallized for hexane, had mp 80°-81° C.; nmr (CDCl3) δ 2.35 (s, 3H), 2.8 (s, 4H), 7.1 (s, 4H); ir (CHCl3) 3540, 3340, 1730, 1165-1 ; Anal Calcd for C12H12F3NO2 : C, 55.60% H, 4.67%; Found: C, 55.41% H, 4.60%.

Aufarbeitung

  1. stirringAfter stirring for 1.5 hr
  2. extractionThe resulting mixtutre was extracted with diethyl ether (3x)
  3. washThe combined ether extracts were washed with water
  4. washwashed with a saturated aqueous solution of NaHCO3
  5. extractionThereafter, the organic extract
  6. dry with materialwas dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1fa0580bc644411981f725437587a388
Quelldatensatz
uspto-grants-1983_10
Patentnummer
US04408077

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