Reaktion #410245

Reaktionsgleichung

3-phenyl phenol

nitric acid

→

2-nitro 5-phenyl phenol

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas consumed
2. 2
   SonstigeThe solution was partitioned between water and methylene chloride
3. 3
   SonstigeThe organic phase was separated
4. 4
   Extraktionthe aqueous phase was extracted once more with methylene chloride
5. 5
   TrocknenThe combined organic phases were dried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)
9. 9
   Sonstigeto afford

Vorschrift

A solution of 3-phenyl phenol (2 g, 11 mmol) in acetic acid was treated with concentrated nitric acid drop-wise until all starting material was consumed. The solution was partitioned between water and methylene chloride. The organic phase was separated and the aqueous phase was extracted once more with methylene chloride. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to afford desired (1.2 g, 50%). 1H NMR (CDCl3): d 10.65(s, 1H), 8.18 (d, 1H, J=10.0 Hz), 7.65 (d, 2H, J=6.0 Hz), 7.49 (m, 3H), 7.34 (s, 1H), 7.10 (d, 1H, J=10.0 Hz).

Quelle