J. Gardner, B. F. Macdonald, H. Maclean
Dec 1, 1960
Citations
0
Influential Citations
22
Citations
Journal
Canadian Journal of Chemistry
Abstract
Plicatic acid, C20H22O10, a polyoxyphenol from western red cedar heartwood, described in a previous paper, has been further characterized by preparation and analysis of additional crystalline derivatives. Crystalline trimethyl and triethyl ethers have been oxidized by alkaline permanganate. The trimethyl ether yielded 3,4,5-trimethoxybenzioc acid, 4,5-di-methoxyphthalic acid (m-hemipinic acid), a pentamethoxy anthraquinone, and a pentamethoxy o-benzoylbenzoic acid which decarboxylated to 3,4,5,3′,4′-pentamethoxy benzophenone. Correspondingly, the triethyl ether gave 3,4-diethoxy-5-methoxybenzoic and 4-ethoxy-5-methoxyphthalic acids, a mixture of pentaalkoxy anthraquinones and a pentaalkoxy o-benzoylbenzoic acid which decarboxylated to 3,3′,4-triethoxy-4′,5-dimethoxy benzophenone identified by cleavage to 3-ethoxy-4-methoxybenzoic and 3,4-diethoxy-5-methoxy-benzoic acids. These results fix the positions of the two methoxyl, three phenolic hydroxyls, and mode of linkage of the two benzene rings. Further evi...