Diformylcresol Explained

Diformylcresol is an organic compound with the formula CH₃C₆H₂(CHO)₂OH. The 2,6-diformyl derivative of p-cresol is the most common isomer and is a white solid at room temperature.

Diformylcresol condenses with amines to give diimines that are widely studied as binucleating ligands.^{[1] [2]}

Synthesis

Formyl groups (aldehydes) are fairly strong deactivating groups for electrophilic aromatic substitution reactions, hence double-addition to a phenol requires forcing conditions. Diformylcresol may be prepared from p-cresol by the Reimer-Tiemann reaction or the Duff reaction.^[3]

The corresponding reaction of phenol would be expected to lead to formylation of the 4-position vs 2,6-selectivity.

Related compounds

• salicylaldehyde, a phenol with only one flanking formyl group

Notes and References

1. 10.1021/IC9514197. Magnetostructural Correlations in Bis(μ₂-phenoxide)-Bridged Macrocyclic Dinuclear Copper(II) Complexes. Influence of Electron-Withdrawing Substituents on Exchange Coupling. 1996. Thompson. Laurence K.. Mandal. Sanat K.. Tandon. Santokh S.. Bridson. John N.. Park. Murray K.. Inorganic Chemistry. 35. 11. 3117–3125. 11666507.
2. 10.1021/ja00404a017. The Synthesis, Redox Properties, and Ligand Binding of Heterobinuclear Transition-Metal Macrocyclic Ligand Complexes. Measurement of an Apparent Delocalization Energy in a Mixed-Valent Cu^ICu^II Complex. 1981. Gagne. R. R.. Spiro. C. L.. Smith. T. J.. Hamann. C. A.. Thies. W. R.. Shiemke. A. D.. Journal of the American Chemical Society. 103. 14. 4073–4081.
3. Lindoy . Leonard F. . Leonard Francis Lindoy . Mono- and Diformylation of 4-Substituted Phenols: A New Application of the Duff Reaction . Synthesis . July 1998 . 1998 . 7 . 1029–1032 . 10.1055/s-1998-2110.