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

HRID 647369

반응식

HRID 647369 반응식
[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]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6386tert-ButanolHCID 516910Potassium nitrite2회HCID 155687561,1,1-Trifluoro-5-(2-methylphenyl)pentan-2-one

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매3회

반응 조건

온도
25 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-1fa0580bc644411981f725437587a388
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04408077

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