Reaktion #216249

Reaktionsgleichung

stearoyl chloride

Meldrum's acid

pyridine

→

methyl 3-oxoeicosanoate

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwas washed with 4N hydrochloric acid
2. 2
   Extraktionthe aqueous phase was back-extracted with methylene chloride
3. 3
   Trocknenthe methylene chloride phase was dried
4. 4
   Einengenconcentrated
5. 5
   workup.STIRRINGstirred
6. 6
   Temperaturunder reflux
7. 7
   TemperaturAfter cooling the separated crystals
8. 8
   Filtrationwere filtered off
9. 9
   workup.DISSOLUTIONdissolved in methylene chloride
10. 10
    Sonstigechromatographed on silica gel with methylene chloride

Vorschrift

270 ml of stearoyl chloride were added dropwise at a maximum of 150° C. to a solution of 117 g of Meldrum's acid and 131 ml of pyridine in 1.51 of methylene chloride. After stirring the reaction mixture was washed with 4N hydrochloric acid, the aqueous phase was back-extracted with methylene chloride and the methylene chloride phase was dried and concentrated. The residue was taken up in methanol and stirred under reflux. After cooling the separated crystals were filtered off, dissolved in methylene chloride and chromatographed on silica gel with methylene chloride. There were obtained 175 g of methyl 3-oxoeicosanoate, m.p. 52°-54° C.

Quelle