Add time:08/29/2019         Source:sciencedirect.com

A Friedel-Crafts condensation of 1,7-dimethoxynaphthalene with the anhydride IV gave a mixture of products from which, after esterification, the ketoesters IX and X could be isolated in 16 and 4·25% yield, respectively. These were hydrogenolysed with PdC to the desoxyesters XI and XII. Cyclodehydration of the latter with an acetic-hydrochloric acid mixture furnished the desired estrahexaene III. Reaction of the lithio derivative of 2-methoxynaphthalene with the dimethyl ester Vc yielded the hydroxyester XVb which was dehydrated to the unsaturated compound XVIII. Assignment of structures to the isomers IX and X by means of mass spectrometry is discussed.

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