PURPOSE: To prepare (11E, 13E)-11,13-hexadecadienal useful as a sex pheromone of grass moth (Oebia undails Fabricius), economically in an industrial scale, in high yield, by heating a specific novel compound in the presence of an alkali, and oxidizing the product.
CONSTITUTION: The objective compound of formula V can be prepared by (1) reacting 3-sulfolene of formula I with 10-tetrahydropyranyloxydecyl halide and an ethyl halide in the presence of a base, (2) treating the resultant compound of formula II (THP is tetrahydropyranyl) with an acid, (3) heating the obtained novel 10-(5-ethyl-3-sulfolen-2-yl)decan-1-ol in the presence of an alkali to obtain the (E,E)-diene alcohol of formula IV in high stereoselective yield, and (4) oxidizing the OH group of the compound with an oxidizing agent.
EFFECT: The objective compound can be prepared in short steps from easily available 3-sulfolene via a novel compound.
YAMADA SACHIKO
SUZUKI TAKAYOSHI
