Baeyer diarylmethane synthesis

What is Baeyer diarylmethane synthesis?

The Baeyer diarylmethane synthesis is a condensation reaction of aromatic compounds with formaldehyde or its derivatives that was first studied by von Baeyer in 1872. In normal conditions, the reactive benzene derivatives, such as phenols and arylamines, are used to condense with formaldehyde, CH2O. However, less-reactive aromatics, including benzene, toluene, benzyl chloride, biphenyl, iodobenzene, naphthalene, and mesitylene, have also been used. Although early studies did not report yields, it is reasonable to expect a 70-80 % yield for this type of reaction.

Baeyer diarylmethane synthesis
Baeyer diarylmethane synthesis

Several other methods have been developed for synthesizing diarylmethanes, such as Katritzky’s benzotriazole method, Kochi’s dealkylative coupling, Fukuzawa’s 1,3-propandiol method, and the reduction method. In general, the condensation occurs at the para-position of substituted aromatics.

References

  • Baeyer, A. (1872), Ueber die Verbindungen der Aldehyde mit den Phenolen. [On the compounds of aldehydes with phenols.] Ber. Dtsch. Chem. Ges., 5: 280-282. https://doi.org/10.1002/cber.18720050186
  • Baeyer, A. (1872), Ueber die Verbindungen der Aldehyde mit den Phenolen und aromatischen Kohlenwasserstoffen. [On the compounds of aldehydes with phenols and aromatic hydrocarbons.] Ber. Dtsch. Chem. Ges., 5: 1094-1100. https://doi.org/10.1002/cber.187200502157
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