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I asked my students to suggest a route of synthesis for 1-phenyl-2-buten-1-one [1], using a Claisen or aldol condensation. One student had the idea of forming the aromatic ring as part of the reaction, something like this (I'm omitting the solvent and the reagents for the elimination step):

cyclisation of highly unsaturated diketone via aldol condensation

This was surprising (I expected an intermolecular condensation reaction between an aromatic molecule and a second molecule).

My question is whether this intramolecular reaction would work in principle (will any of the product be formed?), and whether there are other products (intermolecular, intramolecular) that would be formed at higher yield.

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    $\begingroup$ It would sure work. Very well, I think... Only getting this starting diketone would be harder then the product! Ooopsie, the perils of actual synthesis! That's why questions like that can use some initial constraints. $\endgroup$
    – Mithoron
    Commented May 14 at 20:44
  • $\begingroup$ @Mithoron True, I did not specify that the starting materials should be cheaper than the products, or are smaller molecules. I'm always amazed when everything in a synthetic path works except for removing the protecting group... $\endgroup$
    – Karsten ♦
    Commented May 14 at 20:57

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