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

HRID 437491

反応式

HRID 437491 の反応式
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]

参加物

5

反応物 4

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

生成物 1

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

実験手順

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 assure 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 precipitates 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.

後処理

  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 precipitates
  11. filtrationis collected by filtration and vacuum
  12. customdried at 60° C. overnight
  13. customto give 27 g

出典と根拠

ORDレコード
ord-62ffbd282abb4bf381cafb08434ae911
出典データセット
uspto-grants-1977_06
特許番号
US04031131

関連ノート

読み込み中…