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

Participants

Reaction Conditions

Reaction Steps

1.34 g (10 mmol) of 5-chlorohydantoin and 1.88 g (20 mmol) of phenol were dissolved in 10 ml of dioxane. The solution was then heated to a temperature of 70° C. with stirring for 6 hours. The reaction system was then allowed to cool to room temperature. The reaction system was further cooled over an ice bath for 2 hours. The resulting crystal was recovered by filtration, washed thoroughly with water, and then air-dried to obtain 0.93 g (4.8 mmol; yield: 48%) of 5-(p-hydroxyphenyl)hydantoin in the form of white crystal. The crystal thus obtained exhibited a melting point of 262° to 264°0 C. (decomposition). The IR spectrum, NMR spectrum, and Rf value of thin layer chromatography showed a good conformance to that of a specimen which had been separately synthesized.

Provenance & Evidence