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The female moths of Lepidoptera comprising over 1,000,000 described species possess long-chain unsaturated alcohols or esters as the typical structure of potential sex attractants. In this experiment, various stereoisomers of C_(16)-unsaturated acetates were synthesized for potential sex attractants; e.g., CH₃(CH₂)_m^(++)CH=CH(CH₂)_nOR (m=0-12, n=1-13, R=H and -COCH₃). Seventeen acetates were spectrometrieally examined so that the data would provide a ready catalog of gas chromatography and mass spectrometric data for comparison with natural insect sex attractants. Exclusively cis and traps isomers were obtained by the catalytic and chemical reduction methods, respectively. Commercially available CH₃(CH₂)_mBr, CH₃(CH₂)_mC◎CH, HC◎C(CH₂)_nH and HO(CH₂)_n OH were used for the synthetic starting material. 1-Alkynes, CH₃(CH₂)_m C◎CH exceeding nine methylene groups did not condense with alkyl dihalides. The yield of coupling products was gradually decreased with increasing the molecular weight of diols. In the coupling reaction of BrCH₂CH₂ OTHP with acetylene gas, the tetrahydropyranyl ether of bromohydrin produced undesirable elimination product. In this experiment, it seems that p-toluenesulfonic acid is greatly favoured hydrolyzing agent over dilute sulfuric acid in the hydrolysis of the tetrahydropyranyl ether of long-chain alkynols.
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