Hydrochloric Acid → Isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate
Reaktionsgleichung
[H-].[Na+].[CH3:3][C:4]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][C:10](OC)=[O:11].O.Cl.[CH:23]([OH:26])([CH3:25])[CH3:24]>>[CH3:3][C:4]([CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:5][CH2:6][CH2:7][C:8](=[O:14])[CH2:9][C:10]([O:26][CH:23]([CH3:25])[CH3:24])=[O:11]Komponenten
Versuchsvorschrift
A solution of 1.92 g of sodium hydride in 200 ml of isopropanol was added to a boiling mixture of 10 g of the product of Example 3 and 200 ml of isopropanol and the volume was held constant by replacing proportionately the distillate with isopropanol for 2 hours. After cooling, the mixture was poured into water and acidified with concentrated hydrochloric acid. The mixture was extracted with ethyl acetate and the extract was washed with water, dried over sodium sulfate and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 9-1 petroleum ether (b.p.= 40°-75° C.)-ethyl ether mixture to obtain 7.05 g of isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate in the form of an amber oil with a refractive index of nD24 = 1.467.
Aufarbeitung
- customfor 2 hours
- temperatureAfter cooling
- extractionThe mixture was extracted with ethyl acetate
- washthe extract was washed with water
- dry with materialdried over sodium sulfate
- customevaporated to dryness
- customThe residue was chromatographed over silica
- washwas eluted with a 9-1 petroleum ether (b.p.= 40°-75° C.)-ethyl ether mixture
Quellen und Nachweise
- ORD-Eintrag
- ord-cf8458b1f1734c778fa9defa19dc2a9e
- Quelldatensatz
- uspto-grants-1977_06
- Patentnummer
- US04028386
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