1. Suggested Production of a Guaiacyl Benzofuran Derivative from Softwood via Lignocresol.
- Author
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Hiroshi Nonaka, Ryota Yamamoto, Hirotaka Katsuzaki, and Masamitsu Funaoka
- Subjects
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BENZOFURAN , *HETEROCYCLIC compound derivatives , *SOFTWOOD , *SULFURIC acid , *PHASE separation , *CHEMICAL yield , *REACTIVITY (Chemistry) - Abstract
Lignocresol was isolated from softwood with p-cresol using sulfuric acid and phase separation. An alkaline treatment of the lignocresol, followed by acidification, selectively yielded a guaiacyl coumaran, G1, in the acidsoluble fraction. With further alkaline treatment of G1 in 0.5 M of NaOH solution at 170 °C for 60 min, it was strongly suggested that a guaiacyl benzofuran derivative, G2, was obtained by the elimination of formaldehyde, based on analytical data of the reaction mixture. The process is very unique and well-designed based on the reactivity of Cα-ethers, or Ca-OH, Cß-aryl-ethers, and Cα-OH of lignin, although condensation reactions via formaldehyde occurred in parallel to give condensed products with a diarylmethane structure. Because these phenolic dimers, G1 and G2, were recovered from the guaiacyl unit linked with the neighboring guaiacyl units via two β-aryl-ether bonds, they are promising lignin-derived chemicals that are obtainable in a high yield. [ABSTRACT FROM AUTHOR]
- Published
- 2016
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