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The metathesis of alkenes is a well‐established reaction that is applied in various commercial processes. The meta‐thesis of functionalized olefins has not yet been commercialized despite its considerable potential. The conversion of oleochemical feedstocks into specialty chemicals appears especially attractive. In this paper, a process scheme is proposed for the production of 1,18‐dimethyl octadecanedioate from pure methyl oleate by metathesis. The chemical and technological bottlenecks are explored, and a rough economic evaluation of this route is given. From these considerations, it is concluded that such a process for the metathesis of functionalized alkenes could be viable only if certain conditions are met. Rapid catalyst deactivation is identified as one of the main obstacles. Feedstock purity, efficient recycling of unreacted feed and multiple catalyst regeneration are crucial for economic feasibility. Rhenium‐based catalysts are to be preferred over molybdenum ones because their activation is easier and regenerability is superior. Finally, the direction for future technological and catalysis research is given based upon the results of this work.