反应详情

To a solution of 4-phenoxyphenol (10.0 g, 54 mmol) in 100 mL AcOH was added slowly dropwise nitric acid (69-70%, 3.2 mL, 54 mmol) over about 3 min from an addition funnel. The reaction became warm and was cooled with a water bath. After 1 h, the reaction was poured onto ice and allowed to warm to rt. A gummy solid resulted, which was partitioned between MTBE and water. The organic layer was washed 1× water, 1× brine, dried over sodium sulfate, filtered, and concentrated to a dark oil. This was adsorbed onto 36 g silica gel and dried, and purified in two parts by silica gel chromatography, ISCO, 0-10% EtOAC/hexanes. Product-containing fractions were combined and concentrated to give 2-nitro-4-phenoxyphenol as an orange oil. MS (ESI) m/z: Calculated: 231.1; Observed: 230.0 (M−−1).

1. temperatureThe reaction became warm
2. temperaturewas cooled with a water bath
3. additionthe reaction was poured onto ice
4. customA gummy solid resulted
5. customwhich was partitioned between MTBE and water
6. washThe organic layer was washed 1× water, 1× brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to a dark oil
10. customdried
11. custompurified in two parts by silica gel chromatography, ISCO, 0-10% EtOAC/hexanes
12. concentrationconcentrated