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

Temperature

80 °C

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.

1. additionintroduced
2. temperatureto cool to room temperature
3. customThe dissolved chlorine was then removed
4. additionby introducing nitrogen into the reaction system
5. temperatureThe reaction mixture was then heated to a temperature of 70° C. for 8 hours
6. temperatureto cool to room temperature
7. concentrationThe reaction solution was then concentrated under reduced pressure
8. distillationto distill off acetic acid and phenol
9. additionTo the resulting residue was then added 50 ml of water
10. temperatureThe mixture was then heated
11. dissolutiondissolution
12. filtrationThe resulting precipitate was recovered by filtration
13. washwashed with water
14. customdried

ORD record

ord-193eb380b281497988800f839fd58e90

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05606071