Furan compounds. VII. Rearrangement of 2-acylbenzofuran derivatives into chromonols was written by Ocskay, G.;Vargha, L.. And the article was included in Tetrahedron in 1958.HPLC of Formula: 1646-27-1 This article mentions the following:
The reactions of anti-(a) = and syn-(b)-2-benzofuryl ketoxime p-tolylsulfonates, 2-(p-MeC6H4SO3N:CR)C8H5O (R = Me; Ph) (Ia, Ib; IIa, IIb) with EtOH and MeOH proceed according to their configurations. The anti derivatives Ia, IIa afford chromonoles, IIb undergoes Beckmann rearrangement, and Ib remains unchanged. IIa (15.4 g.) refluxed 2.5 hrs. in 123 ml. MeOH and 12 ml. H2O and the solution kept overnight, the orange solution evaporated in vacuo and the residue taken up in 100 ml. Et2O and 50 ml. H2O, the H2O layer extracted with Et2O, and evaporated gave 5.8 g. p-MeC6H4SO3NH4 (III). The combined Et2O solutions extracted 7 times with 40 ml. 5% NaHCO3 solution and the alk. extract acidified gave a small amount of benzoylcoumaronone (IV) (cf. Geissman and Armen, C.A. 50, 2561b). The Et2O solution extracted 10 times with 40 ml. N NaOH and the alk. extract acidified with 5N H2SO4 gave 1.45 g. flavonol (V), m. 168°. The Et2O solution evaporated and the residue distilled, the distillate (5.2 g., b0.2 147-9°) crystallized (dilute alc.), and recrystallized (petr. ether) gave 2-phenylchromanone 3-dimethylacetal, m. 113-14°; oxime (VI), m. 191° (aqueous Me2CO). VI (0.4 g.) heated 2 hrs. on a steam bath in 5 ml. alc. and 5 ml. 2N H2SO4 and the mixture kept overnight at room temperature gave 80% V. IIb (12 g.) heated 3 hrs. on a steam bath with 96 ml. MeOH and 8 ml. H2O and the mixture evaporated in vacuo, the residue taken up in 100 ml. Et2O and 22 ml. H2O, the acidic aqueous solution neutralized with NH4OH to yield 70% III, and the Et2O layer (containing no IV or V) evaporated gave 1.6 g. 2-benzofurancarboxylic acid anilide, m. 156-7°. The residue from evaporation of the alc. mother liquor distilled in vacuo gave 2.7 g. Me 2-benzofurancarboxylate, m. 50-1°, saponified with 2N NaOH and the hydrolyzate acidified, filtered, and the precipitate recrystallized (C6H6) giving authentic coumarilic acid. Ib (0.6 g.) refluxed in 95% alc. gave 93% Ib after 16 hrs. ad 17% unchanged Ib after 10 days together with 58% III. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1HPLC of Formula: 1646-27-1).
Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.HPLC of Formula: 1646-27-1
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem