High Quality Content by WIKIPEDIA articles! Acyloin condensation is a reductive coupling of two carboxylic esters using metallic sodium to yield an ?-hydroxyketone, also known as an acyloin. The reaction is most successful when R is aliphatic and inert. To achieve the condensation, the chemist should employ aprotic solvents with a high boiling point, such as benzene and toluene. (Usage of protic solvents results in the Bouveault-Blanc reduction.) Depending on ring size and steric properties, but independent from high dilution, the acyloin condensation of diesters favours intramolecular cyclisation over intermolecular polymerisation.

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