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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 and Meredith, G and 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, 60 (11). pp. 848-849. ISSN 0004-9425

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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 hydroxy toluene 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
Keywords: Pheromone, BHT, triene, synthesis, cuprate, anti-oxidant
Journal or Publication Title: Australian Journal of Chemistry
Page Range: pp. 848-849
ISSN: 0004-9425
Identification Number - DOI: 10.1071/CH07223
Additional Information:

Definitive version available at: http://www.publish.csiro.au/nid/51.htm

Date Deposited: 28 Mar 2008 03:49
Last Modified: 18 Nov 2014 03:32
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