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Use of the anti-oxidant Butylated Hydroxytoluene in situ for the synthesis of readily oxidized compounds: application to the synthesis of the moth pheromone (Z,Z,Z)-3,6,9-Nonadecatriene

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Davies, NW, Meredith, G, Molesworth, PP and Smith, JA 2007 , 'Use of the anti-oxidant Butylated Hydroxytoluene in situ for the synthesis of readily oxidized compounds: application to the synthesis of the moth pheromone (Z,Z,Z)-3,6,9-Nonadecatriene' , Australian Journal of Chemistry, vol. 60, no. 11 , pp. 848-849 , doi: 10.1071/CH07223.

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Abstract

The triene (Z,Z,Z)-3,6,9-nonadecatriene was synthesized in three steps from methyl linolenate. The key to the synthesis was the use of the anti-oxidant butylated hydroxytoluene in situ to provide protection of the unstable triene from autoxidation during reaction workup. This simple modification resulted in an increase in the yield from 20 to 85% over three steps.

Item Type: Article
Authors/Creators:Davies, NW and Meredith, G and Molesworth, PP and Smith, JA
Journal or Publication Title: Australian Journal of Chemistry
Publisher: CSIRO Publishing
ISSN: 0004-9425
DOI / ID Number: 10.1071/CH07223
Additional Information:

Copyright © 2007 CSIRO.

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