A convenient one-step synthesis of 2-hydroxy-1,3,5-benzenetricarbaldehyde

The hexamethylenetetramine/trifluoroacetic acid system was demonstrated to be capable of introducing three aldehyde groups into the phenol molecule. Facile, one-step procedures were developed for the preparation of hitherto difficult to synthesize 2-hydroxy-1,3,5-benzenetricarbaldehyde starting from either phenol or 4-hydroxybenzaldehyde. New pKa measurements showed 2-hydroxy-1,3,5-benzenetricarbaldehyde to be an acid stronger than previously reported.