Method for preparing (E3,Z5)-3,5-alkadienyl acetate

Details Method for preparing (E3,Z5)-3,5-alkadienyl acetate Method for preparing (E3,Z5)-3,5-alkadienyl acetate

2008-11-26

2009-12-29

Zucker, Paul A (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

Reexamination Certificate

active

07638647

ABSTRACT:
Provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate and (E3,Z5)-3,5-dodecadienyl acetate which is a sex pheromone of Brazilian apple leafminer. Specifically, provided is a method for preparing (E3,Z5)-3,5-alkadienyl acetate, comprising steps of hydrolyzing 5,5-diethoxy-(Z3)-3-pentenyl methoxymethyl ether in the presence of an acid to obtain 4-formyl-(E3)-butenyl methoxymethyl ether; reacting the 4-formyl-(E3)-butenyl methoxymethyl ether with alkylidene triphenylphosphorane in accordance with the Wittig reaction to obtain (E3,Z5)-3,5-alkadienyl methoxymethyl ether; and obtaining (E3,Z5)-3,5-alkadienyl acetate using the (E3,Z5)-3,5-alkadienyl methoxymethyl ether as a starting substance.

REFERENCES:
Unelius et al., Identification and Synthesis of the Sex Pheromone ofPhtheochroa cranaodes(Lepidoptera: Tortricidae),Tetrahedron Letter, vol. 37, No. 9, pp. 1505-1508 (1996).
Coracini et al., Behavioural effects of minor sex pheromone components in Brazilian apple leafrollerBonagota cranaodes(Lep., Tortricidae),J. Appl. Ent., 127, pp. 427-434 (2003).
Kocienski, “Protecting Groups”, Foundations of Organic Chemistry Series, pp. 22-29, 82-85.

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