6-Chloro-2, 5, 8-trihydroxynaphtho-1, 4-quinone does not undergo cycloaddition reactions but the 1, 2-diacetate, 2-chloro-5, 6-diacetoxy-8-hydroxynaphtho-1, 4-quinone, formed by acetylation-aided tautomerism added (E)-and (Z)-3-alkoxycarbonyl-2, 4-bis (trimethylsiyloxy) penta-1, 3-diene to afford kermesic acid after hydrolysis.