Acid catalyzed aldol condensations of ketones with glyoxylic acid: A simple single-step synthesis of 4-oxo-2,5-heptdienedioic acids

Abstract

The acid catalyzed condensations of ketones with glyoxylic acid at 80 °C, under neat conditions gives 4-oxo-2,5-heptdienedioic acids in 56–88% yield. The solid state photochemical dimerization of 4-oxo-2,5-heptdienedioic acid under UV light gives 2,7-dioxo-tricyclo[6.2.0.0^3,6]decane-4,5,9,10-tetracarboxylic acid in 90% yield.

Keywords:

• Aldol condensation
• cyclobutane
• dienedioic acid
• glyoxylic acid
• ketone
• photocycloaddition