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

Participants

Reaction Conditions

Reaction Steps

2.00 g (20 mmol) of hydantoin was dissolved in 30 ml of acetic acid. The solution was then heated to a temperature of 80° C. under stirring with chlorine being introduced thereinto for 5 hours. The reaction system was then allowed to cool to room temperature. The dissolved chlorine was then removed by introducing nitrogen into the reaction system. To the reaction solution was then added 3.76 g (40 mmol) of phenol. The reaction mixture was then heated to a temperature of 70° C. for 8 hours. The reaction solution was then allowed to cool to room temperature. The reaction solution was then concentrated under reduced pressure to distill off acetic acid and phenol. To the resulting residue was then added 50 ml of water. The mixture was then heated to effect dissolution. The solution was then allowed to stand. The resulting precipitate was recovered by filtration, washed with water, and then dried to obtain 0.55 g (2.89 mmol; yield: 28.9%) of 5-(p-hydroxyphenyl)hydantoin in the form of white flake crystal.

Provenance & Evidence