The interaction between vanilmandelic and L-ascorbic acids led to a cyclopent-2-en-one derivative, whereas the reaction of methyl vanilmandelate with L-ascorbic acid yielded 2- furancarboxylic acid as the major product. The model 3-substituted 4-hydroxybenzyl alcohols and L-ascorbic acid produced ascorbigen-type structures, which easily decarboxylated to give mixtures of the corresponding l-aryl-l-deoxyketoses.