Reaktion #524057

Reaktionsgleichung

hydrochloric acid

isopropanol

sodium hydride

product

methyl 7,11-dimethyl-3-oxo-6,10-dodecadienoate

isopropanol

isopropanol

water

→

isopropyl 7,11dimethyl-3-oxo-6,10-dodecadienoate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefor 2 hours
2. 2
   TemperaturAfter cooling
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate
4. 4
   Waschenthe extract was washed with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   Sonstigeevaporated to dryness
7. 7
   SonstigeThe residue was chromatographed over silica
8. 8
   Waschenwas eluted with a 9-1 petroleum ether (b.p.= 40°-75° C.)-ethyl ether mixture

Vorschrift

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.

Quelle