Phthalide → HCID 20369812, compound

Participants

Reaction Steps

To a stirred suspension of 9.6 g. (0.2 mole) of a 50% dispersion of sodium hydride in mineral oil in 60 ml. of dimethylformamide is added dropwise a solution of 28.8 g. (0.2 mole) of 2-naphthol in 100 ml. of dimethylformamide at such a rate that the temperature does not exceed 25° C. After hydrogen evolution is complete, 26.8 g. (0.2 mole) of phthalide in 100 ml. of dimethylformamide is added dropwise and the stirred mixture is heated under reflux for 2 hours. The solvent is distilled off and the residue is diluted with ice-water. The mixture is extracted with ether and then the aqueous portion is made acidic with 12 N hydrochloric acid. The crystalline precipitate is filtered and recrystallized from aqueous ethanol, using decolorizing carbon to give 2-(2-carboxybenzyloxy)naphthalene.

Provenance & Evidence