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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.00 g (40 mmol) of hydantoin, 6.4 g (40 mmol) of bromine, 0.01 g of methanesulfonic acid, and 30 ml of dioxane was heated to a temperature of 100° C. with stirring for 3 minutes. The reaction mixture was further stirred at a temperature of 50° C. until bromine disappeared. To the reaction mixture was then added 7.52 g (80 mmol) of phenol. The reaction mixture was then heated to a temperature of 50° C. with stirring for 4 hours. The reaction mixture was then allowed to cool to room temperature. The reaction mixture 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 4.69 g (24.4 mmol; yield: 61%) of 5-(p-hydroxyphenyl)-hydantoin in the form of white crystal.

Provenance & Evidence