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

HRID 236075Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 236075
[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>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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 27360731-(2,5-Bis(2,2,2-trifluoroethoxy)phenyl)ethan-1-oneAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of 4,367 kilograms (32.75 moles) of aluminum chloride and 8.8 liters of dichloromethane at 0° C. is added gradually a solution of 3,267 kilograms of 1,4-bis(2,2,2-trifluoroethoxy)benzene and 1.399 kilograms (13.7 moles) of acetic anhydride in 1.3 liters of dichloromethane. The reaction temperature is maintained at 5° to 10° C. while stirring the mixture for about 16 hours. The reaction mixture is then heated to its reflux temperature and maintained under reflux for 4 hours. The reaction mixture is then acidified with 8.76 kilograms of 10 percent hydrochloric acid. Ice is added to the mixture to maintain the temperature below 20° C. The organic layer is separated and the aqueous layers are extracted several times with dichloromethane. The organic layers are dried, then evaporated to provide a residue which is triturated with hexane to provide a yellow solid product. Two crops of product are obtained providing a total yield of 3.088 kilograms of 2,5-bis(2,2,2-trifluoroethoxy)acetophenone, m.p. 84° to 88° C., yield 82 percent.

Aufarbeitung

  1. temperatureThe reaction temperature is maintained at 5° to 10° C.
  2. temperatureThe reaction mixture is then heated to its
  3. temperaturereflux temperature
  4. temperaturemaintained
  5. temperatureunder reflux for 4 hours
  6. additionIce is added to the mixture
  7. temperatureto maintain the temperature below 20° C
  8. customThe organic layer is separated
  9. extractionthe aqueous layers are extracted several times with dichloromethane
  10. customThe organic layers are dried
  11. customevaporated
  12. customto provide a residue which
  13. customis triturated with hexane
  14. customto provide a yellow solid product
  15. customTwo crops of product are obtained

Quellen und Nachweise

ORD-Eintrag
ord-39939b9ad55e415f928413e19e472999
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04642384

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