Experimental studies of Lewis acid catalyzed additions of long chained alcohols to activated 1,4-benzoquinone

Article abstract of DOI:10.1016/S0040-4020(97)10409-4

Lewis acid promoted additions of long chained alcohols to 2- carbomethoxy-1,4-benzoquinone (1) have been examined by using various LAs; AlCl₃, TiCl₄, MgBr₂ and MgCl₂. It has been found that the bidentate Lewis acid MgCl₂, having ability to coordinate to both carbonyl oxygens (chelate control) of 2-carbomethoxy-1,4-benzoquinone (1), produced the addition product almost quantitatively at mild conditions. The MgCl₂ catalyzed additions of alcohols have been utilized in the synthesis of rare 2- alkoxyhydroquinones (7a-e). The reactions between quinone 1, alcohol and AlCl₃ or TiCl₄ have also been investigated by using NMR spectroscopy.