Reaktion #7004

Reaktionsgleichung

3-chloro-4-methoxy aniline

H2SO4

NaNO2

→

3-chloro-4-methoxy phenol

Ausbeute 30.0%

Lösungsmittel

H2O

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 0° C.
2. 2
   Temperaturthe black solution was then heated
3. 3
   Temperaturto reflux for 30 min
4. 4
   ExtraktionThe mixture was extracted with EtOAc (4×50 mL)
5. 5
   Einengenthe combined extracts were concentrated in vacuo
6. 6
   SonstigeThe residue was chromatographed (SiO2; 4:1 hex:EtOAc)

Vorschrift

To a 0° C. solution of 3-chloro-4-methoxy aniline (1.0 g; 6.4 mmol) in 1:1 H2O:conc. H2SO4 (100 mL) was added very slowly a solution of NaNO2 (0.5 g; 7.6 mmol) in H2O (10 mL). Thick yellow fumes were emitted, and the black solution was then heated to reflux for 30 min. The mixture was extracted with EtOAc (4×50 mL) and the combined extracts were concentrated in vacuo. The residue was chromatographed (SiO2; 4:1 hex:EtOAc) to obtain 3-chloro-4-methoxy phenol (300 mg; 30%) as a yellow oil.

Quelle