Phenol → 5-(4-Hydroxyphenyl)imidazolidine-2,4-dione

Participants

Reaction Conditions

Reaction Steps

4.0 g (40 mmol) of hydantoin, 10 ml of dioxane, and 2.0 ml (40 mmol) of bromine were mixed at room temperature. The reaction mixture was then vigorously stirred at a temperature of 100° C. for 30 minutes. The reaction mixture was then cooled to a temperature of 0° C. To the reaction mixture was then added 5.7 g (60 mmol) of phenol. The reaction mixture was then allowed to undergo reaction at a temperature of 0° C. for 12 hours. The resulting precipitate was recovered by filtration, washed with water, and then dried to obtain 5.53 g (yield: 72%) of 5-(p-hydroxy-phenyl)hydantoin. The crystal thus obtained exhibited a melting point of 263° to 265° C. The infrared spectrum, NMR spectrum and Rf value of silica gel thin layer chromatography of the crystal showed a complete conformance to that of a specimen synthesized by the method as disclosed in JP-B-55-22474.

Provenance & Evidence