PREPARATION OF 2-PROPARGYL-3-METHYL-4-HYDROXY-2- CYCLOPENTENONE

PURPOSE:To prepare the titled compound useful as an intermediate of agricultural chemicals, pharmaceuticals and perfumery, economically from practical viewpoint, by cyclizing cis-3-nonene-2,5-dion-8-yne at a specific temperature in the presence of water and a basic catalyst. CONSTITUTION:2-Propargyl...

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Bibliographic Details
Main Authors SAITOU KENJI, YAMACHIKA HIROSHI, TAKIZAWA YUKIHISA, KOUNO NOBUHARU
Format Patent
LanguageEnglish
Published 12.01.1984
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
CHEMISTRY
METALLURGY
ORGANIC CHEMISTRY
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Summary:PURPOSE:To prepare the titled compound useful as an intermediate of agricultural chemicals, pharmaceuticals and perfumery, economically from practical viewpoint, by cyclizing cis-3-nonene-2,5-dion-8-yne at a specific temperature in the presence of water and a basic catalyst. CONSTITUTION:2-Propargyl -3- methyl -4-hydroxy-2-cyclopentenone of formula IIuseful as an intermediate of prostaglandin (a drug), jasmone (perfumery), etc., is prepared by cyclizing cis-3-nonene-2,5-dion-8-yne of formula I at <=0 deg.C in the presence of water and a basic catalyst. Since the compound of formula I can be prepared easily by the ring-opening reaction of 2-methyl-5-(3-butenyl)-furan of formula III with an oxidizing agent especially chromium (VI)-organic base complex at <=0 deg.C, the compound of formula III is obtained easily and economically in an industrial scale by combining the above reaction with the ring-closing reaction.
Bibliography:Application Number: JP19820113456