Formation of Carbon-Linked Anthrone-Lignin and Anthrahydroquinone-Lignin Adducts

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Abstract
The quinone methide from guaiacylglycol-β-guaiacyl ether [l-(3-methoxy-4-hydroxyphenyl)-2-(2-methoxyphenoxy)ethanol] formed carbon-carbon bonded adducts with both anthrone and anthrahydroquinone (AHQ). It was found that the anthrone adduct [l-(3-methoxy-4-hydroxyphenyl)-1-(anthracen-9-one-10-yl)-2-(2-methoxyphenoxy)ethane] was much more resistant to alkaline degradation than the corresponding AHQ-adduct Jl-(3-methoxy-4-hydroxyphenyl)-l-(10-hydroxyanthracen-9-one-10-yl)-2-(2-methoxyphenoxy)ethane]. It was demonstrated, by NMR spectroscopy that analogous anthrone and AHQ adducts formed with milled wood lignin and had relative alkaline stabilities consistent with those observed with the model adducts. At 10° C the AHQ-lignin adduct partially decomposed to the Y-monoacetates of coniferyl alcohol and p_-coumaryl alcohol which subsequently reacted with excess AHQ to give the novel adducts, trans-1-(3-methoxy-4-hydroxyphenyl)-3-(10-hydroxyanthracen-9-one-10-yl)propene, and trans-1-(4-hydroxyphenyl)-3-(10-hydroxyanthracen-9-one-10-yl) propene, respectively.

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