5-Methyl-2-hexanone → 3-Chloro-2-isobutyl-but-2-enal
Reaktionsgleichung
P(Cl)(Cl)([Cl:3])=O.[CH3:6][CH:7]([CH3:13])[CH2:8][CH2:9][C:10](=[O:12])C.[CH3:14][C:15]([O-])=O.[Na+]>CN(C=O)C>[Cl:3][C:15]([CH3:14])=[C:9]([CH2:8][CH:7]([CH3:6])[CH3:13])[CH:10]=[O:12]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 5 °C
Versuchsvorschrift
Phosphorusoxychloride (53.7 g, 350 mmol) is slowly added to DMF (60 mL) stirred at 5° C. Upon complete addition, the clear solution is stirred for further 30 min at 5° C. before 5-methyl-2-hexanone (20 g, 175 mmol) is added dropwise. The yellow solution is stirred for 30 min at 0° C., then for 90 min at rt. The mixture becomes warm (40° C.) and a thick suspension forms. The mixture is cooled to 25° C. and stirring is continued for 1 h before it is poured into an aq. solution of NaOAc (80 g)/ice mixture. The mixture is extracted twice with diethyl ether. The organic extracts are washed with water, combined, dried over MgSO4, filtered and evaporated to give crude 3-chloro-2-isobutyl-but-2-enal (35.4 g) as a yellow oil, LC-MS: tR=0.97 min.
Aufarbeitung
- additionUpon complete addition
- additionis added dropwise
- stirringThe yellow solution is stirred for 30 min at 0° C.
- temperatureThe mixture becomes warm (40° C.)
- temperatureThe mixture is cooled to 25° C.
- stirringstirring
- waitis continued for 1 h before it
- extractionThe mixture is extracted twice with diethyl ether
- washThe organic extracts are washed with water
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Quellen und Nachweise
- ORD-Eintrag
- ord-0c9bccf4b12b414da79762c9ba2603e2
- Quelldatensatz
- uspto-grants-2011_08
- Patentnummer
- US08003800B2
Notizen zur Reaktion
Wird geladen…