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On phthalides and 1,3-indandiones. LIV. The synthesis of 3-(2-alkyloxy-1-naphthylmethylene)phthalides and 2-(2-alkyloxy-l-naphthyl)-1,3-indandiones

M. Lácová and A. Komínek

Department of Organic Chemistry and Biochemistry, Faculty of Natural Sciences, Komenský University, 801 00 Bratislava


Abstract: The synthesis of new derivatives of phthalides and 1,3-indandiones starting from 2-alkyloxy-l-naphthylacetic acids or the corresponding nitriles is described. It has been found that nitriles, under conditions of the Gabriel modification of the Perkin synthesis, react at 260°C similarly as the corresponding acids. The 3-(2-alkyloxy-l-naphthylmethylene)phthalides thus formed undergo rearrangement to furnish 2-(2-alkyloxy-1-naphthyl)-1,3- - indandiones. 1 - Chloromethyl - 2 - alky loxy naphthalenes, bis(2-alkyloxy-1 - -naphthyl)methanes, 2-alkyloxy-l-naphthylacetonitriles, and 2-(2-methylpropoxy)- 1-naphthylacetic acid were the intermediates hitherto not reported.

Full paper in Portable Document Format: 274a536.pdf


Chemical Papers 27 (4) 536–543 (1973)

Sunday, October 20, 2019

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