Cross-metathesis of fatty acid methyl esters with acrolein: An entry to a variety of bifunctional compounds

The cross‐metathesis of renewable fatty acid methyl esters with acrolein was investigated. The bifunctional formyl‐esters obtained are interesting compounds for further transformations into bifunctional polymer precursors. Several experimental parameters and ruthenium catalysts have been evaluated. Best results were obtained with thermally pre‐treated fatty acid methyl esters (FAMEs). The reactions performed with high efficiency with low catalyst loadings allowing TONs as high at 1000. An acetal protected acrolein was also used, enabling improvement of the reaction performances. A tandem cross‐metathesis/hydrogenation reaction without isolation of the formyl intermediate delivered the expected alcohol ester in good yield. Practical applications: The cross‐metathesis of FAMEs with acrolein provides access to a broad range of bifunctional compounds of interest for the manufacture of polymers, considering the multiple post‐transformations of the formyl group available The ruthenium‐catalyzed cross‐metathesis of fatty acid methyl esters with acrolein is presented. The bifunctional formyl‐esters are valuable precursors for subsequent transformations such as the tandem cross‐metathesis/hydrogenation reaction delivering a hydroxyl‐ester in one step. The ruthenium‐catalyzed cross‐metathesis of fatty acid methyl esters with acrolein is presented. The bifunctional formyl‐esters are valuable precursors for subsequent transformations such as the tandem cross‐metathesis/hydrogenation reaction delivering a hydroxyl‐ester in one step.