Synthesis of Biphenols Containing Anhydride,Imido, or Dicyano Arylene Moieties

The novel biphenols, 3,6-bis(4-hydroxyphenyl)phthalic anhydride (2) and 3,6-bis(4-hydroxyphenyl)benzene-1,2-dicarbonitrile (15) were synthesized. Reaction of trans-anethole (4-propenylanisole) (6) with the Schiff base 7 yielded l,4-bis((4-methoxyphenyl)-l,3-butadiene (8). Diels-Alder reactions with maleic anhydride or fumaronitrile followed by dehydrogenation and demethylation gave the corresponding biphenols in good yields (ca. 73%). Reaction of 2 with primary amines yields the corresponding imides.