Reaktion #65596

Reaktionsgleichung

4-chloro-1-naphthol

3-chloro-2,5-dimethyl-1-nitrobenzene

potassium carbonate

→

3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethyl-1-nitrobenzene

Ausbeute 47.5%

Lösungsmittel

dimethylsulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturmaintained at that temperature for a period of 6 hours
2. 2
   FiltrationThe reaction mixture was then filtered
3. 3
   workup.ADDITIONthe filtrate was diluted with 20 milliliters of methanol
4. 4
   Temperaturto cool to room temperature
5. 5
   SonstigeCrystallization
6. 6
   workup.WAIToccurred during this cooling period
7. 7
   TemperaturThe filtrate was further cooled in an ice bath
8. 8
   Filtrationfiltered
9. 9
   Waschenthe collected crystals washed with cold methanol
10. 10
    SonstigeRecrystallization from a hexane-ethyl acetate mixture

Vorschrift

Into a solution containing 9.10 grams (51.1 mmol) of 4-chloro-1-naphthol and 10.12 grams (46.0 mmol) of 3-chloro-2,5-dimethyl-1-nitrobenzene in 22 milliliters of dimethylsulfoxide at room temperature and under a nitrogen atmosphere was added 8.89 grams (64.4 mmol) of anhydrous potassium carbonate. The resulting mixture was heated to a temperature of 130° C. and maintained at that temperature for a period of 6 hours. The reaction mixture was then filtered and the filtrate was diluted with 20 milliliters of methanol and allowed to cool to room temperature. Crystallization occurred during this cooling period. The filtrate was further cooled in an ice bath, filtered and the collected crystals washed with cold methanol. Recrystallization from a hexane-ethyl acetate mixture afforded 7.92 grams of 3-chloro-4-(4-chloro-1-naphthoxy)-2,5-dimethyl-1-nitrobenzene as a white solid having a melting point of 135° C.-137° C.

Quelle