p-Toluenesulfonic acid → 5-(1-Cyclopentenyl)pentan-2-one

HRID 2185163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2185163
[C:1]1(=[CH:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CC(OC)(C)C>[C:1]1([CH2:6][CH2:7][CH2:8][C:9](=[O:11])[CH3:10])[CH2:5][CH2:4][CH2:3][CH:2]=1

Komponenten

5

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 135280135-Cyclopentylidenepentan-2-one

Produkt 1

HCID 135280095-(1-Cyclopentenyl)pentan-2-oneAusbeute 72,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5-cyclopentylidene-2-pentanone (9.92 g; 65 mmol) and p-TsOH (100 mg; 0.53 mmol) in toluene (150 ml) was heated at 90° C. for 8 hours, then cooled down to room temperature, diluted with MTBE (100 ml), washed with saturated NaHCO3 (50 ml), H2O (50 ml), brine (50 ml), dried over MgSO4 and concentrated in vacuo. Distillation under reduced pressure (48° C./0.065 torr) yielded 7.13 g of 5-(cyclopent-1-enyl)-2-pentanone (purity about 80%), which was further purified by flash chromatography to give 6.1 g (61% yield) of a 89% pure product containing 11% of 5-cyclopentylidene-2-pentanone.

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. washwashed with saturated NaHCO3 (50 ml), H2O (50 ml), brine (50 ml)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. distillationDistillation under reduced pressure (48° C./0.065 torr)

Quellen und Nachweise

ORD-Eintrag
ord-74036c35ea5443259811297d2d5a8373
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399811B1

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