Crossed Aldol Condensation (CAC) as a Feasible Route for Synthesis of a 1, 2-Unsaturated Carbonyl Compound-1,3 Diphenylpropenone

We here report an optimized crossed aldol method for synthesis of 1,2-unsaturated carbonyl compound, 1,3-diphenylpropenone (82-93% yield) rely on alcoholic base assisted condensation of arylmethyl ketone with aromatic aldehydes.

The method simply follows the conventional synthetic route however an extraordinary control over various reaction parameters enhance its synthetic practicability.

Furthermore, a comparative study has been done to explore the scope for synthesis of 1,3-diphenylpropenone by crossed aldol reaction by solvent assisted method (SAM) and solvent-less method (SLM). Undeniably, solvent-less technique (90-95% yield) hold superiority however tuning of certain reaction parameters, leveled-up solvent assisted crossed aldol reaction, but not to an analogues platform.

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Crossed Aldol Condensation (CAC) as a Feasible Route for Synthesis of a 1, 2-Unsaturated Carbonyl Compound-1,3 Diphenylpropenone

Acrolein, acrylic acid, crotonaldehyde, crotonic acid, ethyl crotonate, isocrotonic acid, fumeric acid, maleic acid, maleic anhydride, methyl acrylate are few examples of compounds bearing 1,2-unsaturated carbonyl functionality, characterized by presence of keto-ethylenic moiety separated by a single C-C bond.

This unique configuration assigns the molecule an reactive double bond amenable to get attack by nucleophile at 1st as well 2nd position however 2nd predominate leading to formation of 1,4 addition type product. Synthetically, the 1,2-unsaturated carbonyl compounds can be synthesize by numerous synthetic pathways, aldol reaction among meritoriously distinguished.

Aldol condensation represents an important class of selfcondensing reactions providing unique synthetic platform for yielding 1,2-unsaturated carbonyl compounds, further chemically modified as per applicability. 

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