Pyran series, its analogs, and related compounds. XXXV. Reaction of 4-chlorocoumarin and sodium alcoholates was written by Zagorevskii, V. A.;Savel’ev, V. L.;Dudykina, N. V.. And the article was included in Khim. Geterotsikl. Soedin. in 1970.HPLC of Formula: 1646-27-1 This article mentions the following:
Reaction of 4-chlorocoumarin (I) with NaOH in aqueous dioxane at 20° gave 92.5% (o-hydroxyphenyl)-propiolic acid (II); under reflux the reaction gave 80% benzofuran-2-carboxylic acid (III). II was hydrogenated over Pd/BaSO4 to give 81% (o-hydroxyphenyl)propionic acid. II, heated with aqueous NaOH, gave 83% III. I, treated with NaOMe in MeOH at 20°, gave 95.6% 4-methoxycoumarin (IV); at 70° the reaction gave 91.1% IV and 7.5% III. I with MeONa in MeOH-dioxane gave 64% IV, 17% III, and 12% III Me ester. Reaction of I with EtONa in EtOH at 70° gave 38% 4-ethoxycoumarin (V), 11% III, and 31.6% III Et ester (VI). In EtOH-dioxane the reaction gave 17.4% V, 7.5% III, and 48% VI. I with PhONa in dioxane gave 85% 4-phenoxycoumarin and 13% II. I with Me2NCH2CH2ONa in PhMe gave 15% (as HCl salt) 2-(dimethylamino)ethoxy]coumarin, ester (VII) of III, 15% III, and 18% 4-[2-(dimethylamino)ethoxy]coumarin, which with concentrated HCl gave 4-hydroxycoumarin; VII.HCl similarly gave III. V treated with EtONa in EtOH-dioxane gave 24% 4-hydroxycoumarin and traces of VI; analogous results were obtained in EtOH alone. 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. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.HPLC of Formula: 1646-27-1
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem