Abstract

A process is disclosed for preparing a mixture of 8E,10E-dodecadienol (Ia), 8E,10Z-dodecadienol (Ib), 8Z,10E-dodecadienol (Ic) and 8Z,10Z-dodecadienol (Id), H3C-CH=CH-CH=CH-(CH2)6-CH2-OH, (8E,10E = Ia), (8E,10Z = Ib), (8Z,10E = Ic), (8Z,10Z = Id) from 1,8-octandiol (II) which is transformed by a halogenating agent into (III): Hal-CH2-(CH2)6-CH2-OH, (III) is then reacted with (IV): H2C=CH-O-R, producing (V): Hal-CH2-(CH2)6-CH2-O-CH(CH3)-OR, which is transformed in the presence of magnesium with crotonaldehyde into (VI): H3C-CH=CH-CH(OH)-(CH2)8-O-CH(CH3)-OR. The alcohol protective group is split off from (VI) in the presence of an acid, at the same time as the hydroxyl function is eliminated. Also disclosed are intermediates for this process, and a process for fighting the fruit surface eating tortrix moth Cydia pomonella with this mixture according to the mating interruption method.

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