An α-diketone from the condensation product of glucose and ethyl acetoacetate

Abstract

When the product from the condensation of glucose and ethyl acetoacetate, ethyl 2-D-arabino-tetrahydroxybutyl-5-methyl-4-furoate (Ia), is heated in ethanolic hydrogen chloride, an a-diketone (IVa) is produced. It exists as a mono-enol in solution and in the solid state. Although this diketone is formed with an aliphatic side chain, there is at first a predominant, but reversible, cyclization to the "difuran" (II). With hydrogen peroxide the diketone yields 2-carboxymethy1-5- methyl-4-furoic acid (VII), and with alkali it undergoes a benzilic acid rearrangement.