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Official Journal of the Japan Wood Research Society

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Simple method for synthesizing phenolicβ-O-4 dilignols

Abstract

A modified synthetic method for phenolicβ-O-4 lignin substructure model dimers was developed involving protection of the phenolic hydroxyl group of acetophenons with benzoyl chloride, bromination with 4-dimethylaminopyridiniumbromide perbromide, condensation with phenols in the presence of 18-crown-6-ether, condensation with paraformaldehyde, reduction with NaBH4 and debenzoylation. This method results in shorter reaction times and increasing yields without the application of strict anhydrous and drastic conditions or chloric solvents. This alternative route could be applied to theβ-O-4 dilignol syntheses of four combinations of guaiacyl and syringyl derivatives.

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Correspondence to Shingo Kawai.

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Kawai, S., Okita, K., Sugishita, K. et al. Simple method for synthesizing phenolicβ-O-4 dilignols. J Wood Sci 45, 440–443 (1999). https://doi.org/10.1007/BF01177919

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Key words

  • β-O-4 Dilignols
  • Chemical synthesis
  • Chloric solvents
  • Anhydrous condition
  • Mild condition