Water → 1,1,1-Trifluoro-2-phenyl-5-methyl-hexa-2,4-diene

HRID 67128

Reaktionsgleichung

Reaktionsgleichung von HRID 67128
C([Li])CCC.[Br-].[CH3:7][C:8]([CH3:30])=[CH:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:31][C:32]([F:42])([F:41])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=O.O>CCCCCC.O1CCCC1>[F:31][C:32]([F:42])([F:41])[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[CH:10][CH:9]=[C:8]([CH3:30])[CH3:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 99052,2,2-TrifluoroacetophenoneHCID 3083722(3-Methylbut-2-enyl)triphenylphosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 537780391,1,1-Trifluoro-2-phenyl-5-methyl-hexa-2,4-dieneAusbeute 56,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

65 ml of 15% strength solution of n-butyl-lithium in hexane were added dropwise to a suspension of 41.1 g (0.1 mol) of dry 3,3-dimethylallyl-triphenyl-phosphonium bromide in 300 ml of anhydrous tetrahydrofuran at 0° C. under nitrogen, while stirring. The deep red solution thus obtained was stirred at 0° C. for a further 15 minutes and 17.4 g (0.1 mol) of ≃,≃,≃-trifluoroacetophenone were then added dropwise at 0°-10° C. The mixture was subsequently stirred at room temperature until it was decolorized (about 12 hours). 600 ml of water were then added and the reaction mixture was extracted 5 times with 200 ml of petroleum ether each time. The petroleum ether phases were dried over magnesium sulphate and the solvent was then stripped off in a rotary evaporator under a waterpump vacuum. 150 ml of n-hexane were added to the residue and residual triphenyl-phosphine oxide was filtered off. The solvent was subsequently distilled off from the filtrate under normal pressure and the oily residue was then distilled in vacuo. 12.8 g (56.6% of theory) of 1,1,1-trifluoro-2-phenyl-5-methyl-hexa-2,4-diene were obtained as a slightly reddish liquid with a boiling point of 80°-85° C. under 3 mbar.

Aufarbeitung

  1. customThe deep red solution thus obtained
  2. stirringwas stirred at 0° C. for a further 15 minutes
  3. stirringThe mixture was subsequently stirred at room temperature until it
  4. custom(about 12 hours)
  5. extractionthe reaction mixture was extracted 5 times with 200 ml of petroleum ether each time
  6. dry with materialThe petroleum ether phases were dried over magnesium sulphate
  7. customthe solvent was then stripped off in a rotary evaporator under a waterpump vacuum
  8. addition150 ml of n-hexane were added to the residue and residual triphenyl-phosphine oxide
  9. filtrationwas filtered off
  10. distillationThe solvent was subsequently distilled off from the filtrate under normal pressure
  11. distillationthe oily residue was then distilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6b0f43275b54e96b3774dc604e5bc7a
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04344963

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