Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization

p-Alkoxy phenol (p-AOPs) compounds were obtained by one-step selective hydroxylation of alkoxyl-aryl ethers with the transition metal ruthenium(II) as catalyst and [bis(trifluoroacetoxy)iodo]benzene (PIFA) as oxidant. These p-AOPs could be easily converted to quinone monoacetals (QMAs) after dearomatization. Condensation of the QMAs with ss-naphthols provided polycyclic benzofurans which have a wide application prospect. The protocol established in this paper offered a facile and reliable way for the synthesis of these important compounds.

Automated summary

p-Alkoxy phenol (p-AOPs) compounds were obtained by one-step selective hydroxylation of alkoxyl-aryl ethers with the transition metal ruthenium(II) as catalyst and [bis(trifluoroacetoxy)iodo]benzene (PIFA) as oxidant. These p-AOPs could be easily converted to quinone monoacetals (QMAs) after dearomatization. Condensation of the QMAs with ss-naphthols provided polycyclic benzofurans which have a wide application prospect. The protocol established in this paper offered a facile and reliable way for the synthesis of these important compounds.