Process for preparing 11-tetradecenal insect pheromone

Details Process for preparing 11-tetradecenal insect pheromone Process for preparing 11-tetradecenal insect pheromone

C - Chemistry, Metallurgy

07

C

260/568.1, 260/6

C07C 43/14 (2006.01) A01N 35/02 (2006.01) C07C 41/56 (2006.01) C07C 43/313 (2006.01) C07C 45/40 (2006.01) C07C 45/51 (2006.01) C07C 47/14 (2006.01) C07C 47/20 (2006.01) C07F 3/02 (2006.01)

Patent

CA 1077059

ABSTRACT The specification discloses a novel process for the preparation of 11-tetradecenal and novel intermediates therefor. There is also disclosed processes for the intermediates. The novel intermediates include 1,1-dialkoxy-9-halo-nonane and 1,1- dialkoxy-11-tetradecene There is further disclosed a process for preparing a mixture of cis- and trans-11-tetradecenal at the molec- ular ratio of approximately 1-cis-form to 9 trans-form, by react- ing a Grignard reagent of 1,1-dialkoxy-9-halo-nonane with a mixture (approximately 60:40) of 1-chloro-2-pentene and 3-chloro- 1-pentene and thereafter hydrolyzing thus formed 1,1-dialkoxy- 11-tetradecene. 11-Tetradecenal is useful as a sex pheromone against the female eastern spruce budworm (Choristoneura fumiferana). The 9:1 ratio of trans/cis isomers is believed to be the most effective ratio to use against the budworms.

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