Synthesis of 12-acetoxy-1,3-dodecadiene, an insect sex pheromone of the red bollworm moth, from a butadiene telomer was written by Mandai, T.;Yasuda, H.;Kaito, M.;Tsuji, J.;Yamaoka, R.;Fukami, H.. And the article was included in Tetrahedron in 1979.Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate The following contents are mentioned in the article:
Selective hydroboration of R(CH2)3CH:CHCH2OPh (I; R = CH2:CH), prepared in 78% yield by Pd-catalyzed telomerization of butadiene with PhOH, followed by H2O2 oxidation, gave 80% I (R = HOCH2CH2). Tosylation (84%) of the latter followed by treatment with NaI in refluxing Me2CO gave 95% I (R = ICH2CH2). Grignard reaction of the latter with RO(CH2)4MgCl (R = tetrahydropyranyl) gave 80% RO(CH2)9CH:CHCH2OPh (II; R as before), which after hydrolysis and acetylation gave II (R = AcO). The title pheromone was obtained (71%) by Pd-catalyzed elimination of PhOH from II (R = AcO). This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate).
(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics