A study was made of the reductive cleavage of the lignin models 1-(4-hydroxy-3-methoxyphenyl)-2-o-methoxyphenoxy-1,3-propanediol and 4'-hydroxy-3'-methoxy-2-o-methoxyphenoxyacetophenone. In cleavage with sodium in liquid ammonia at −33° from the first we obtained pyrocatechol, guaiacol, 4-propylguaiacol, and 1- and 3-(4-hydroxy-3-methoxyphenyl)-1-propanols, and from the second we obtained guaiacol and 4-hydroxy-3-methoxy-α-methylbenzyl alcohol.
The formation of the same products in this reaction from fir lignin and from 1-(4-hydroxy-3-methoxyphenyl)-2-o-methoxyphenoxy-1,3-propanediol indicates the presence in lignin of “uncondensed” structures of the 1-(4-hydroxy-3-methoxyphenyl)-2-(aryloxy)-1,3-propanediol type.
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Semechkina, A.F., Shorygina, N.N. Decomposition of lignin models with a solution of sodium in liquid ammonia. Russ Chem Bull 13, 826–830 (1964). https://doi.org/10.1007/BF00846498