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Simple method for synthesizing phenolicβ-O-4 dilignols

Journal of Wood Science volume 45, pages 440–443 (1999)Cite this article

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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Author notes

  1. Kyoko Okita

    Present address: Yutaka Foods Co., 470-2395, Taketoyo, Aichi, Japan

  2. Kazuhiro Sugishita

    Present address: YMC Co., 923-8557, Komatsu, Ishikawa, Japan

  3. Ai Tanaka

    Present address: Kato Chemicals Co., 470-2409, Taketoyo, Aichi, Japan

Authors and Affiliations

  1. Department of Applied Bioorganic Chemistry, Faculty of Agriculture, Gifu University, 501-1193, Yanagido, Gifu, Japan

    Shingo Kawai, Kyoko Okita, Kazuhiro Sugishita, Ai Tanaka & Hideo Ohash

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  1. Shingo Kawai
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  2. Kyoko Okita
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  3. Kazuhiro Sugishita
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  4. Ai Tanaka
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  5. Hideo Ohash
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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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