Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid

Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7-oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and...

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Bibliographic Details
Published inChemistry of natural compounds Vol. 39; no. 1; pp. 28 - 30
Main Authors Ishmuratov, GY, Yakovleva, MP, Botsman, LP, Ishmuratova, NM, Muslukhov, RR, Khambalova, GV, Tolstikov, GA
Format Journal Article
LanguageEnglish
Published NEW YORK Springer Nature 01.01.2003
Subjects
Chemistry
Chemistry, Medicinal
Chemistry, Organic
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Physical Sciences
Science & Technology
Doebner and Tishchenko reactions
7-oxooct-1-ylacetate
9-oxo-2E-decenoic acid
7-oxooctanoic acid
7-oxooctanal
pheromone
7-oxooctyl-7-oxooctanoate
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Summary:Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7-oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and 7-oxooctanoic acid).
ISSN:0009-3130
1573-8388
DOI:10.1023/A:1024172327822