Hydrochloric Acid → 1-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-one

HRID 236074

反応式

HRID 236074 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]([F:22])([F:21])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:11][CH:10]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24].Cl>CCCCCC.ClCCl>[CH3:24][C:23]([C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:6]([F:21])([F:22])[F:5])[CH:14]=[CH:13][C:12]=1[O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[O:25]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 7371561,4-Bis(2,2,2-trifluoroethoxy)benzeneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 27360731-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-one収率 90%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8058Hexane溶媒

実験手順

To a mixture of 2.43 moles (324 g.) of aluminum chloride in 648 ml. of dichloromethane is added a solution of 0.88 mole (274 g.) of 1,4-bis(2,2,2-trifluoroethoxy)benzene and 0.97 mole (92 ml.) of acetic anhydride in 880 ml. of dichloromethane over a 3 hour period while maintaining the temperature at above 0° C. The reaction mixture is then heated to its reflux temperature and stirred at reflux for 5 hours. The progress of the reaction is followed using thin-layer chromatography. The reaction mixture is placed in an ice bath and ice and 10 percent hydrochloric acid are added slowly to decompose the aluminum chloride complex. The temperature of the reaction mixture is not allowed to exceed 25° C. The organic phase is separated and washed once with 2 liters of 10 percent hydrochloric acid and then with 2 liters of water. The combined aqueous phase is extracted with several liters of dichloromethane. The organic phase is dried over magnesium sulfate, then evaporated to provide a moist residue. Hexane is added to the residue and the resulting solid is collected by filtration and washed with hexane. Upon drying, 250 g. of light yellow crystalline 2,5-bis(2,2,2-trifluoroethoxy)acetophenone is obtained. The yield is 90 percent, the m.p. is 84° to 86° C.

後処理

  1. temperatureThe reaction mixture is then heated to its
  2. temperaturereflux temperature
  3. temperatureat reflux for 5 hours
  4. customThe reaction mixture is placed in an ice bath
  5. customto exceed 25° C
  6. customThe organic phase is separated
  7. washwashed once with 2 liters of 10 percent hydrochloric acid
  8. extractionThe combined aqueous phase is extracted with several liters of dichloromethane
  9. dry with materialThe organic phase is dried over magnesium sulfate
  10. customevaporated
  11. customto provide a moist residue
  12. filtrationthe resulting solid is collected by filtration
  13. washwashed with hexane
  14. customUpon drying

出典と根拠

ORDレコード
ord-f7ec070462b641cbb6d46d534985f8bc
出典データセット
uspto-grants-1987_02
特許番号
US04642384

関連ノート

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