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Synthesis of Insect Pheromone: (Z)-3-dodecenyl acetate
Monoalkenyl acetates are used as one of lepidopteran pheromone components. However, (Z)-3-alkenylacetate as pheromone components is rarely known. Among them, (Z)-3-dodecenylacetate is used as pheromone components of Aproaerema anthyllidella and Tecia solanivora. Recently, (Z)-3-dodecenylacetate was identified as one of pheromone components for an insect pest in Korea (unpublisheddata). For the demand of development of mating disruption against thepest, large amount of (Z)-3-dodecenylacetate (Z3-C12Ac) was needed. Here, we reported the synthetic procedures for (Z)-3-decenylacetate (Z3-C12AC). The Grignard reagent from 1-decyne and ethyl magnesium bromide was reacted with ethylene oxide in dry tetrahydrofuran (THF). Thus synthesized 3-dodecyn-1-ol was reduced to (Z)-3-dodecen-1-ol (Z3-C12OH) by hydrogenation over Lindlar’s catalyst. The alcohol was acetylated to desired (Z)-3-dodecenylacetate (Z3-12Ac) with acetic anhydride by general procedures. The yield was 62.6% through the all procedures. Thepurity was 98.0% (by GC-MS). The isomeric purity was >99% (by NMR).
