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

HRID 65330

반응식

HRID 65330 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 pH1 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-2a58d7c8fe124c55a04851a5b30f523b
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04613360

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