Preparation, intermediates for the preparation and the use of a mixture of dodecdienol isomers

摘要

A process 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) starting from 1,8-octanediol (II) which is converted with a halogenating agent into (III)Hal-CH2-(CH2)6-CH2-OH(III)where (III) is subsequently reacted with (IV),H2C=CH-O-R(IV)to give (V)Hal-CH2-(CH2)6-CH2-O-CH(CH3)-OR(V),(V) is converted in the presence of magnesium and crotonaldehyde into (VI)H3C-CH=CH-CH(OH)-(CH2)8-O-CH(CH3)-OR(VI)and the protective group R and the hydroxyl group are simultaneously eliminated from (VI) in the presence of acid, novel intermediates for this process, and methods for controlling the codling moth Cydia pomonella by interfering with mating using this mixture are described.