Synthesis of cis-jasmone via the retroaldol-aldol condensation of 3-(cis-3-hexenyl)-2-cyclopentenone in an autoclave.
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概要
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<I>cis</I>-Jasmone was efficiently synthesized from 2-cyclopentenone. The treatment of 2-cyclopentenone with sodium <I>p</I>-toluenesulfinate gave 3-(<I>p</I>-tolylsulfonyl)cyclopentanone in a 92.5% yield. The alkylation of the sulfone, after the protection of the ketone, with <I>cis</I>-1-bromo-3-hexene, followed by desulfonylation with 5% hydrochloric acid in tetrahydrofuran, afforded 3-(<I>cis</I>-3-hexenyl)-2-cyclopentenone in a good yield. The retroaldol-aldol condensation of the cyclopentenone in a stainless steel autoclave in presence of 5% sodium hydroxide yielded <I>cis</I>-jasmone in a 80% yield.
- 公益社団法人 日本化学会の論文
著者
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Yoshida Takashi
Department Of Agriculture Kyoto University
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Saito Shojiro
Department Of Industrial Chemistry Shibaura Institute Of Technology
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