Acetic Acid → n-Butyl cyclopentadiene

HRID 566626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 566626
Br[CH2:2][CH2:3][CH2:4][CH3:5].[C:6](O)(=O)[CH3:7].[CH2:10]1[CH2:14]OC[CH2:11]1>>[CH2:2]([C:7]1[CH2:6][CH:11]=[CH:10][CH:14]=1)[CH2:3][CH2:4][CH3:5]

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 8002Butyl bromide2×HCID 8028Tetrahydrofuran2×

Produkt 1

HCID 102598n-Butyl cyclopentadieneAusbeute 70 %

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

A solution of bromobutane (0.98 mol) in 28 grams of THF is heated to 60-65° C. A warm solution of CpMgCl in THF (1.0 mol) as produced in Example 1 is added to the bromobutane solution while maintaining a pot temperature between 60-65° C. After the addition and the consequent reaction are complete by GC analysis, the reaction mixture is cooled to ambient temperature, 25% by weight of aqueous acetic acid is added, and the organic layer is separated, washed with 10% by weight of aqueous sodium carbonate, and dried over anhydrous sodium sulfate. The organic layer is filtered, and fractionally distilled under reduced pressure to recover 70 to 80% yield of n-butyl cyclopentadiene.

Aufarbeitung

  1. additionAfter the addition
  2. customthe consequent reaction
  3. temperaturethe reaction mixture is cooled to ambient temperature
  4. customthe organic layer is separated
  5. washwashed with 10% by weight of aqueous sodium carbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe organic layer is filtered
  8. distillationfractionally distilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18cc523239b140f1a8815624cee47894
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06175027B1

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