Aldol condenstation: Synthesis of dibenzalacetone


The aldol condensation of benzaldehyde and acetone is a textbook example of an exothermic, spontaneous reaction which is often performed during practical courses at universities and high schools. Due to its exothermic character, the reaction vessel is traditionally cooled in an ice bath, with controlled reagent addition to avoid the formation of side products and evaporation of acetone. The product dibenzalacetone is used as a UV blocker and as a ligand in organometallic chemistry.

Aldol condensation of benzaldehyde and acetone to dibenzalacetone

Aldol condensation of benzaldehyde and acetone to dibenzalacetone

To avoid the use of cooling and controlled reagent addition, FutureChemistry has translated this reaction from a batch process to a continuous flow process. FutureChemistry’s typical three-tier approach led to a protocol which can be adapted to any viable aldol condensation:

       1) Translation of batch process to continuous flow process:
           a) Stock solutions approach, yielding a homogeneous reaction mixture.
           b) Quenching solution to follow the reaction in time.
           c) Flow markers approach to accurately assess reaction parameters.
      2) Automated reaction optimisation.
      3) Out scaling to preparative synthesis

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