The Alkaline Hydrolysis of Some Lignin Model 2-Arylcoumarans

Abstract

Reaction of the 2-arylcoumaran (2b) with 2b sodium hydroxide at 170� gave predominantly the (E)- and (2)-stilbenes (4a) and (5a) in the ratio 1 : 2, and the 2-arylbenzofuran (6) as a minor product. The isomeric 1,2-diarylpropan-1-ols (7b) and (8b) were prepared and gave on treatment with 2N sodium hydroxide at 170� an analogous mixture of stilbene isomers to that obtained from the coumaran (2b). The mechanism of formation of compounds (4a), (5a), and (6) is discussed.