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Hydroxymethylphenylnaphthoie acid lactones
Author(s) -
Ahmed Riaz,
Holmes T. L.,
Stevenson Robert
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110504
Subject(s) - chemistry , hydroxymethyl , lactone , lithium aluminium hydride , aluminum hydride , acetic anhydride , catalysis , ether , organic chemistry , acetic acid , dicarboxylic acid , zinc , catalytic hydrogenation , dehydrogenation , medicinal chemistry , methoxide
Reduction of 1‐phenylnaphthalene‐2,3‐dicarboxylic anhydride (I) with zinc and acetic acid or lithium aluminium hydride yields a mixture of 1‐phenyl‐3‐hydroxymethyl‐2‐naphthoie acid lactone (II) and 1‐phonyl‐2‐hydroxymethyl‐3‐naphthoie acid lactone (III). Catalytic hydrogenation of (I) gave the tetrahydronaphthalene dicarboxylic anhydride (IV). Oxidation of the phenyldihydronaphthofuran (X), prepared by base‐catalyzed cyclization of the ether (IX), also yielded lactones (II) and (III). The phenyltetrahydronaphthofuran (XII) was similarly prepared by cyclization of the phenylpropargyl cinnamyl ether (XI).