Dimethyl Sulfoxide → 3-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid

HRID 27318

반응식

HRID 27318 반응식
CS(C)=O.[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1Cl.[C:17](=[O:20])([O-])[O-:18].[K+].[K+].[OH2:23]>>[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1[O:23][C:6]1[CH:11]=[C:10]([CH:9]=[CH:8][CH:7]=1)[C:17]([OH:18])=[O:20]

참가 물질

5

반응물 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 94813,4-DichlorobenzotrifluorideHCID 11430Potassium Carbonate

생성물 1

HCID 916853-[2-Chloro-4-(trifluoromethyl)phenoxy]benzoic acid수율 85%

실험 절차

To a 300 ml. 3-necked flask fitted with a magnetic stirring bar, condenser, drying tube and thermometer is charged the solid from above dimethylsulfoxide (100 ml), 3,4-dichlorobenzotrifluoride (21.5 g. 0.10 mole) and anhydrous potassium carbonate (5.0 g) to asure an alkaline pH. The reaction temperature is taken rapidly to 138°-44° C. while vigorous stirring is maintained. After 4 hours a significant conversion is realized and heating is continued overnight (total 22 hrs.). The reaction mixture is then cooled to room temperature and poured into water (1000 ml) and the aqueous reaction mixture extracted with CCl4 (200 ml). The aqueous layer is then decanted and acidified to pH 1 with concentrated hydrochloric acid. The white solid that precipitated is collected by filtration and vacuum dried at 60° C. overnight to give 27 g of an off-white solid 3-(2-chloro-4-trifluoromethylphenoxy)benzoic acid (85% yield), mp 124°-5° C.

후처리

  1. custom3-necked flask fitted with a magnetic stirring bar, condenser
  2. customdrying tube
  3. customis taken rapidly to 138°-44° C.
  4. temperatureis maintained
  5. temperatureheating
  6. waitis continued overnight
  7. custom(total 22 hrs.)
  8. extractionthe aqueous reaction mixture extracted with CCl4 (200 ml)
  9. customThe aqueous layer is then decanted
  10. customThe white solid that precipitated
  11. filtrationis collected by filtration and vacuum
  12. customdried at 60° C. overnight

출처 및 근거

ORD 기록
ord-3709ba55304248f79537e0fe843734f9
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220468

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