Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1978-11-16
1980-07-15
Lone, Werren B.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C07C 4720
Patent
active
042128307
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 molecular ratio of approximately 1-cis-form to 9 trans-form, by reacting 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.
REFERENCES:
patent: 3821421 (1974-06-01), Bergeman et al.
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