4'-Fluoroacetophenone → 1,1-Bis[4-(4-acetylphenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane

HRID 6195

反応式

HRID 6195 の反応式
C(=O)([O-])[O-:2].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1.C1[CH:37]=[C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40](O)[CH:39]=2)C(O)=CC=1.[CH3:46][C:47]([C:49]1[CH:54]=[CH:53][C:52](F)=[CH:51][CH:50]=1)=[O:48]>>[C:47]([C:49]1[CH:54]=[CH:53][C:52]([O:31][C:28]2[CH:27]=[CH:26][C:25]([C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:7][C:41]4[CH:40]=[CH:39][C:38]([C:36](=[O:2])[CH3:37])=[CH:43][CH:42]=4)=[CH:9][CH:10]=3)([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([F:16])([F:17])[F:18])=[CH:30][CH:29]=2)=[CH:51][CH:50]=1)(=[O:48])[CH3:46]

参加物

5

反応物 4

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 33665(1,1'-Biphenyl)-2,3'-diol2 回HCID 190051754,4'-(2,2,2-Trifluoro-1-phenylethane-1,1-diyl)diphenol

生成物 1

HCID 152191841,1-Bis[4-(4-acetylphenoxy)phenyl]-1-phenyl-2,2,2-trifluoroethane

実験手順

A suspension of 15.2 grams (0.11 moles) anhydrous potassium carbonate in 370 milliliters of N2N'-dimethylacetamide is prepared in a 1 liter, 2-necked round bottom flask equipped with a reflux condensor and a nitrogen gas inlet. To the suspension is added 16.61 grams (0.05 moles) of 1,1-bis-(4-hydroxyphenyl)-1-phenyl-2,2,2-trifluoroethane) using a powder additional funnel against a counter current of nitrogen gas, as heat is gradually applied via a heating mantle. Next 18.26 milliliters (0.15 moles, 3 equivalents relative to the diphenol) of commercially obtained 4- fluoroacetophenone is added via a syringe to the heated solution. The solution is refluxed and stirred for 48 hours, at which time no diphenol is evident by thin layer chromatography (elution with 2:1 hexanes:ethyl acetate). The quantity of solvent is reduced to approximately 200 milliliters by distillation, whereupon the solution is cooled, and poured into approximately 500 milliliters of 1M HCL. The product precipitates as an off white granular solid. About 10 grams of the crude product is dissolved in dichloromethane and loaded onto a chromatography column using TLC grade silica. The product is obtained in pure form by eluting the column with a mixture of dichloromethane:hexanes in a 4:1 ratio.

後処理

  1. customis prepared in a 1 liter, 2-necked round bottom flask
  2. customequipped with a reflux condensor and a nitrogen gas inlet
  3. temperatureas heat
  4. temperatureThe solution is refluxed
  5. washis evident by thin layer chromatography (elution with 2:1 hexanes:ethyl acetate)
  6. distillationThe quantity of solvent is reduced to approximately 200 milliliters by distillation, whereupon the solution
  7. temperatureis cooled
  8. additionpoured into approximately 500 milliliters of 1M HCL
  9. customThe product precipitates as an off white granular solid
  10. dissolutionAbout 10 grams of the crude product is dissolved in dichloromethane
  11. customThe product is obtained in pure form
  12. washby eluting the column
  13. additionwith a mixture of dichloromethane

出典と根拠

ORDレコード
ord-68af85f3122543a7bc6f77f268cb1285
出典データセット
uspto-grants-1993_09
特許番号
US05247050

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