Intramolecular cyclization of 2-hydroxycinnamaldehydes

✍ Scribed by Yu. M. Chunaev; N. M. Przhiyalgovskaya; L. N. Kurkovskaya

• Book ID: 104782666
• Publisher: Springer US
• Year: 1988
• Tongue: English
• Weight: 499 KB
• Volume: 24
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00478854

✦ Synopsis

2t2 (III~). This compound was similarly obtained from 0.20 g (0.70 =mole) of u-methyl-3-bromo-5-nitro-2-hydroxycinnamaldehyde.

The product was purified with a column packed with silica gel by elution with carbon tetrachloride-ether (3:1). The yield of a7yellowish crystalline powder (from chloroform-~thanol) was 0.18 g (Rf 0.78). IR spectrum: 1525, 1348 cm-* (NO2).

2-Ethoxy-3-methyl-6-nitro-8-bromo-2H-chromene (IVy)

. A 0.15-g (0.52 mmole) sample of aldehyde Ij was refluxed in 30 ml of ethanol for 6 h, after which the solvent was evaporated and 5 ml of hexane was added to the residue. The resulting yellowish crystals were removed by filtration and washed with hexane to give 0.14 g of product.

IR spectrum: 1530, 1340 cm ~* (NO2).