Reaktion #410271

Reaktionsgleichung

sodium nitrite

sodium nitrate

2-cyanophenol

sulfuric acid

→

desired product

Ausbeute 42.7%

2-nitro-6-cyanophenol

Ausbeute 42.7%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with water
2. 2
   TrocknenThe organic layer was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   SonstigeThe solvent was evaporated

Vorschrift

2-cyanophenol (2.38 g, 20 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.88 g, 22 mmol). The addition of sulfuric acid (20 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2Cl2) gave the desired product(1.4 g, 42%). 1H NMR (CD3COCD3): d 8.47 (d,1H), 8.15 (d, 1H), 7.30 (t, 1H).

Quelle