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

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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Official URL: http://dx.doi.org/10.1071/CH07223

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
Additional Information:	Definitive version available at: http://www.publish.csiro.au/nid/51.htm
Keywords:	Pheromone, BHT, triene, synthesis, cuprate, anti-oxidant
ID Code:	3563
Deposited By:	Dr Jason A Smith
Deposited On:	28 Mar 2008 14:49
Last Modified:	18 Jul 2008 20:42
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