Zhou Yong-chang
2005
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Journal
Journal of Shenyang Institute of Chemical Technology
Abstract
3-methyl-2-hydroxy-cyclopent-2-en-1-one was prepared from ethyl propionate and dietthyl oxalate through Claisen ester condensation, Michael addition, Dieckmann ester condensation and decarboxylation reactions in total 51.09 % yield. The intermediate 2-methyl-3-oxo-butanedioic acid diethyl ester (Ⅰ) was synthesized in 81.58 % yield by Claisen ester condensation at temperature 60 ℃, reaction time 3 h and n(ethyl propionate)∶n(diethyl oxolate)=1∶1.2. The optimum conditions of Michael addition and Dieckmann ester condesation reactions were temperature 80 ℃, reaction time 7.5 h and (n(Ⅰ):n(ethyl acrylate))=1∶1.8. The final product was obtained by decarboxylation with H_3PO_4([w(H_3PO_4)=50 %]) as catalyst. Its molecular structure was identified by IR and ~1H-NMR analysis.