Reaktion #310535

Reaktionsgleichung

potassium iodide

6-amino-2,2-dimethyl-7-nitro-2H-benzo[b]pyran

Nitrosyl sulphuric acid

sodium nitrite

→

2,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran

Ausbeute 39.4%

Lösungsmittel

water

water

acetic acid

sulphuric acid

Toluene

sulphuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturbeing warmed
2. 2
   workup.DISSOLUTIONto dissolved the solid
3. 3
   Temperaturthen re-cooled to approximately 4° C.)
4. 4
   workup.ADDITIONwas added
5. 5
   Sonstigethe temperature of the reaction mixture below 12° C
6. 6
   workup.STIRRINGThe dark, viscous mixture was stirred at approximately 7° C. for a further hour
7. 7
   workup.DISSOLUTIONto dissolve the resulting precipitate
8. 8
   workup.STIRRINGthe mixture stirred in an ice bath for 20 minutes
9. 9
   Sonstigethe organic phase was separated
10. 10
    Waschenwashed with water
11. 11
    Sonstigedried
12. 12
    Sonstigeevaporated in vacuo

Vorschrift

To a cooled solution of 6-amino-2,2-dimethyl-7-nitro-2H-benzo[b]pyran (20.0 g)* in glacial acetic acid (800 ml) was added concentrated sulphuric acid (400 ml) and the solution stirred at 8° C. Nitrosyl sulphuric acid (prepared by dissolving sodium nitrite (6.62 g) in cold concentrated sulphuric acid (200 ml) the mixture being warmed to dissolved the solid then re-cooled to approximately 4° C.) was added keeping the temperature of the reaction mixture below 12° C. The dark, viscous mixture was stirred at approximately 7° C. for a further hour then poured into a cold (approximately 5° C.) solution of potassium iodide (15.27 g) in water (200 ml). Toluene (800 ml) was added to dissolve the resulting precipitate and the mixture stirred in an ice bath for 20 minutes, then at room temperature for 18 hours. The reaction mixture was diluted with water (500 ml), the organic phase was separated, washed with water, dried and evaporated in vacuo to afford the required 2,2-dimethyl-6-iodo-7-nitro-2H-benzo[b]pyran (11.84 g, 39%) as a red gum.

Quelle