An attempt to prepare 3-substituted isocoumarins by the condensation of acid chlorides with homophthalic acid to afford the desired 3-chloromethylisocoumarin was made but surprisingly the desired isocoumarin (8) was not formed. However, a novel 3H-furo[3,4-c]isochromene-1,5-dione (9) was isolated which was characterized by spectroscopy and Xray crystallography. A mechanism for the formation of 3H-furo[3,4-c]isochromene-1,5-dione (9) is also proposed.
Keywords: Acetyl chloride, Chloroacetyl chloride, Homophthalic acid, Novel 3H-furo[3,4-c]isochromene-1,5-dione, isocoumarin, spectroscopy, X-ray crystallography, dihydroisocoumarins, naphthalene, NMR, DMF
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