Reaktion #62900

Reaktionsgleichung

sodium hydride

4,5-dichloro-2-nitrobenzoic acid

hydrochloric acid

4-chlorophenol

→

title compound

4-Chloro-5-(4-chlorophenoxy)-2-nitrobenzoic Acid

Lösungsmittel

diglyme

diglyme

diglyme

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile maintaining the temperature at 10° C
2. 2
   TemperaturThe reaction mixture was then heated to 153° C. (oil bath) for 1 hour
3. 3
   Sonstige45 minutes
4. 4
   TemperaturThe reaction mixture was cooled to room temperature
5. 5
   ExtraktionThe solution was extracted with ethyl acetate
6. 6
   Trocknenthe organic layer dried over anhydrous magnesium sulfate
7. 7
   SonstigeThe solvent was removed
8. 8
   Sonstigethe crude solid triturated with hexane
9. 9
   Sonstigefollowed by recrystallization from carbon tetrachloride

Vorschrift

To 30 ml of dry diglyme under a nitrogen atmosphere was added 0.960 g (0.02 mol) of sodium hydride dispersion in mineral oil (50%). The solution was cooled to 10° C. and 1.28 g (0.01M) 4-chlorophenol in 15 ml of dry diglyme was added dropwise while maintaining the temperature at 10° C. This was followed by the dropwise addition of 2.36 g (0.01 mol) of 4,5-dichloro-2-nitrobenzoic acid in 15 ml of dry diglyme. The reaction mixture was then heated to 153° C. (oil bath) for 1 hour and 45 minutes. The reaction mixture was cooled to room temperature and poured into an ice/water mixture. The pH was then adjusted to 1.5 with 6N hydrochloric acid. The solution was extracted with ethyl acetate, and the organic layer dried over anhydrous magnesium sulfate. The solvent was removed and the crude solid triturated with hexane, followed by recrystallization from carbon tetrachloride to give the title compound: yield 1.65 g (50%) m.p. 160°-162° C.

Quelle