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Phthalides and 1,3-indandiones. VII. 2-(Fluorophenyl)-1,3-indandiones

P. Hrnčiar

Komensky University, Bratislava

Abstract: cf. CA 53, 10149a. Prepn. of 2-(o-, m-, or p-fluorophenyl)-1,3-indandione, m. 149-51°, m. 159-60°, or m. 121-2°, resp., from the corresponding phthalide was described. The corresponding fluorobenzalphthalide (4.8 g.) was heated with 150 ml. MeOH and 0.6 g. Na on the water bath for 1 hr. and neutralized with 20% HCl after cooling. The ppt. of 2-(o- or m-fluorophenyl)-1,3-indandione were crystd. from EtOH and of p-deriv. from CCl₄. The prepn. of o-, m-, or p-fluorophenylacetic acids, m. 64° (water), m. 45° (benzene-petr. ether), or m. 86° (water), was described. The corresponding fluorobenzyl cyanide (27 g.), 30 ml. 96% H₂SO₄ and 18 ml. H₂O was heated and hydrolyzed while boiling 40-60 min. The mixt. was poured into 200 ml. H₂O and the ppt. dissolved in NaHCO₃; the corresponding fluoroacetic acid was pptd. with HCl.

Full paper in Portable Document Format: 142a119.pdf (in Slovak)

Chemical Papers 14 (2) 119–123 (1960)