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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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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 |
|---|---|
| Authors/Creators: | Davies, NW and Meredith, G and Molesworth, PP and Smith, JA |
| Keywords: | Pheromone, BHT, triene, synthesis, cuprate, anti-oxidant |
| Journal or Publication Title: | Australian Journal of Chemistry |
| ISSN: | 0004-9425 |
| DOI / ID Number: | 10.1071/CH07223 |
| Additional Information: | Definitive version available at: http://www.publish.csiro.au/nid/51.htm |
| Item Statistics: | View statistics for this item |
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