The Malonic Ester Synthesis, Organic Chemistry

If you are in organic chemistry II, you will likely cover reactions involving the alpha carbons of carbonyls. These reactions cover a wide range of reactions including the aldol condensation, Claisen condensation, the malonic ester synthesis, the acetoacetic ester synthesis, the Michael reaction, and the Robinson annulation. In this post, we are going to look at the malonic ester synthesis. Join us for a look at the malonic ester synthesis in organic chemistry.

Take a look at generic reaction below:

Overall reaction: malonic ester synthesis

In this reaction, multiple other reactions are needed. First, we need to form an enolate. Notice that the base we use is the same alkoxide of the diethyl malonate ester that we are starting with. We use this so there is no issue with ester hydrolysis. Next, we typically have the enolate attack an alkyl halide in a SN2 reaction, so here we need to worry about having favorable conditions for a SN2 reaction. The next reaction involved is ester hydrolysis under acidic conditions. Finally, to get to the end product, we must undergo a decarboxylation reaction. Ready to learn more about the malonic ester synthsis? Take a look at the video below!

The malonic ester synthesis tutorial