Acetone → 1-[3-(Trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acid

HRID 27280노트

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HRID 27280 반응식
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1.CC(C)=[O:20].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.S(=O)(=O)(O)O>[O-2].[O-2].[O-2].[Cr+6].O>[F:17][C:2]([F:1])([F:16])[C:3]1[CH:4]=[C:5]([N:9]2[CH:13]=[C:12]([C:14]([OH:20])=[O:15])[CH:11]=[N:10]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 233444471-(3-(trifluoromethyl)phenyl)-1H-pyrazole-4-carbaldehydeHCID 131709961Jones' reagent3회

생성물 1

HCID 149944991-[3-(Trifluoromethyl)phenyl]-1H-pyrazole-4-carboxylic acid수율 89%

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 962Water용매

실험 절차

Into a 500 ml. Erlenmeyer flask, fitted with a thermometer and a magnetic stirrer, containing a solution of 8.3 g. (0.0346 M.) of 1-(m-trifluoromethylphenyl)pyrazole-4-carboxaldehyde in 300 ml. of acetone is slowly added 20.0 ml. of Jones reagent (prepared by dissolving 26.7 g. of chromium trioxide in 23.0 ml. of concentrated sulfuric acid and then diluting to 100 ml. with water), the addition of the Jones reagent being effected while the solution is cooled by an ice water bath. Upon completion of the addition of the Jones reagent, the reaction mixture is stirred, under cooling, for 15 minutes and then for an additional 20 minutes at room temperature, after which time it is quenched with a large volume of water and allowed to stand at room temperature for about 3 hours. The resultant precipitated solids are then filtered and washed successively with water and petroleum ether. The solvent is then removed under vacuum to yield 1-(m-trifluoromethylphenyl)pyrazole-4-carboxylic acid, m.p. 145°-148° C. (Yield: 89%).

후처리

  1. customErlenmeyer flask, fitted with a thermometer and a magnetic stirrer
  2. additioncontaining a solution of 8.3 g
  3. dissolutionby dissolving 26.7 g
  4. temperatureis cooled by an ice water bath
  5. temperatureunder cooling, for 15 minutes
  6. customafter which time it is quenched with a large volume of water
  7. waitto stand at room temperature for about 3 hours
  8. customThe resultant precipitated solids
  9. filtrationare then filtered
  10. washwashed successively with water and petroleum ether
  11. customThe solvent is then removed under vacuum

출처 및 근거

ORD 기록
ord-46d183fa0fcb4319a574fea044f921fe
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220792

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