SYNTHESIS OF 12-ACETOXY-1, 3-DODECADIENE, AN INSECT SEX-PHEROMONE OF THE RED BOLLWORM MOTH, FROM A BUTADIENE TELOMER

8-Phenoxy-1, 6-octadiene (1) formed by the Pd-catalyzed telomerization of butadiene with phonol was converted to 8-phenoxy-6-octen-1-ol (3). The alcohol 3 was converted to 8-iodo-1-phenoxy-2-octene (5). The Grignard reagent 7 prepared from 4-chloro 1-butyl tetrahydropranyl ether was coupled with the iodide 5 by the catalysis of CuI and bipyridyl to give 12-phenoxy-10-dodecen-1-ol (9), which was converted to 12-acetoxy-1-phenoxy-2-dodecene (10). Finally, 12-acetoxy-1, 3-dodecadiene (11) was obtained by the palladium catalyzed elimination of phenol from phenoxyacetoxy-dodecene (10). © 1979.