Toluene → 2-Isopentylcyclopent-2-en-1-one

HRID 61331

Reaktionsgleichung

Reaktionsgleichung von HRID 61331
C(O[C:5](=[O:7])[CH3:6])(=O)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1.[C:19]1(C)C=CC=CC=1>>[CH3:19][CH:8]([CH3:18])[CH2:13][CH2:12][C:11]1[C:5](=[O:7])[CH2:6][CH2:9][CH:10]=1

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 7918Acetic Anhydride

Produkt 1

HCID 1224642-Isopentylcyclopent-2-en-1-one

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

2-(3-Methyl-butyllidene)-cyclopentanone (1.093 Kg, 7.19 mol, obtained as detailed above), acetic anhydride (300 mL, 3.17 mol), p-toluenesulfonic acid (PTSA, 10 g), and toluene (500 mL) were charged into a flask and heated to 120-130° C. When gas chromatography analysis indicated the completion of the reaction, the reaction mixture was cooled to room temperature and quenched with Na2CO3 solution (100 mL). The resulting mixture was washed twice with brine (1 L). A rushover process provided the crude product 2-(3-methyl-butyl)-cyclopent-2-enone.

Aufarbeitung

  1. customthe completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. customquenched with Na2CO3 solution (100 mL)
  4. washThe resulting mixture was washed twice with brine (1 L)

Quellen und Nachweise

ORD-Eintrag
ord-f38a1f5c245a4e0ebbe5d8bd9cdd9f36
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09441185B2

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