Journal of Organic Chemistry p. 4658 - 4662 (1981)
Update date:2022-08-03
Topics:
Smith, James G.
Welankiwar, Sudha S.
Chu, Noreen G.
Lai, Eric H.
Sondheimer, Susan J.
A synthetic route to 7-acetoxybenzanthracenes is described based on the generation of 1-benzylisobenzofurans and their capture with methyl acrylate in a Diels-Alder reaction.The 1,4-epoxy-1,2,3,4-tetrahydronaphthalene derivatives so formed are aromatized to naphthoate esters under acidic conditions and hydrolyzed to the naphthoic acids, and these are cyclized to the 7-acetoxybenzanthracenes with zinc chloride in acetic anhydride.
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Doi:10.1039/c39810000550
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