Reaktion #93763

Reaktionsgleichung

phenol

nitric acid

phenol

dichlorophenol

2,3-dichlorophenol

→

4-nitro-2,3-dichlorophenol

Ausbeute 71.0%

Lösungsmittel

acetic acid

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled
2. 2
   workup.ADDITIONhad been added
3. 3
   SonstigeThe yellowish product which precipitated
4. 4
   Sonstigewas collected
5. 5
   TemperaturThe product was heated in a sublimation apparatus over a 4 day period at 80° C. at 4 torr
6. 6
   Sonstigeto remove any 2-nitro-5,6-dichlorophenol
7. 7
   Sonstigeformed as a by-product in the above nitration
8. 8
   SonstigeThe residue was recrystallized from toluene

Vorschrift

A solution was prepared from 200 g of 2,3-dichlorophenol and 540 ml of glacial acetic acid. The solution was cooled, and a solution of 58 ml of 90% nitric acid in 160 ml of glacial acetic acid was added in dropwise fashion with stirring to the solution of the phenol. After half of the solution of the phenol had been added, the reaction mixture was allowed to warm to ambient temperature. It was stirred for 15 minutes at ambient temperature after all of the dichlorophenol had been added. The reaction mixture was then poured over 3,000 ml of an ice/water mixture. The yellowish product which precipitated was collected. The product was heated in a sublimation apparatus over a 4 day period at 80° C. at 4 torr. to remove any 2-nitro-5,6-dichlorophenol formed as a by-product in the above nitration. The residue was recrystallized from toluene to yield 80.3 g of 4-nitro-2,3-dichlorophenol; m.p.=148°-150° C.

Quelle