ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

The preparation of cyclic phthalides and their conversion into derivatives of 1,3-indandione. I. Naphthylphthalide and some of its derivatives

P. Hrnčiar, Ľ. Krasnec, and M. Furdík

Komenský University, Bratislava

Abstract: A prepn. of 3-(1-naphthylmethylene)phthalide (I) and its conversion into 2-(1-naphthyl)-1,3-indandione (II) by MeONa or EtONa in alk. medium are described. II forms small golden-yellow scales, sol. in cold dioxane and cyclohexanone and in warm alc., m. 205°. Br (1 molar equiv.) displaces a H atom in the naphthalene ring of I, giving 3-(5-bromo-1-naphthylmethylene)phthalide (III), m. 226°. Another molar equiv. Br further brominates the double bond; III with MeONa in alk. medium forms 2-(5-bromo-1-naphthyl)-1,3-indandione.

Full paper in Portable Document Format: 101a12.pdf (in Slovak)

Chemical Papers 10 (1) 12–18 (1956)