Reaktion #569894

Reaktionsgleichung

nitric acid

crude product

4-methoxy- benzenesulfonylchloride

nitric acid

→

3-nitro-4-methoxy-benzenesulfonyl-chloride

Ausbeute 89.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo maintain control
2. 2
   Sonstigeover the very vigorous reaction which
3. 3
   Sonstigeto react completely (i.e.
4. 4
   workup.ADDITIONwas added
5. 5
   workup.ADDITIONWhen addition
6. 6
   ExtraktionThe resulting slurry was extracted with CH2Cl (3×250 ml)
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   SonstigeThe solvent was removed in a rotary evaporator
10. 10
    Sonstigethe yellow crystals thus obtained
11. 11
    Sonstigewere recrystallized from 50% Et2O/hexane

Vorschrift

350 ml of fuming nitric acid (8.3 mol) was added very carefully in 25 ml aliquots to the crude product of Example 1 in a one-liter flask. To maintain control over the very vigorous reaction which immediately commenced, each portion of the nitric acid was allowed to react completely (i.e., until no fumes were evolved) before the next portion was added. When addition was complete, the solution was allowed to stand at room temperature for 30 minutes and then carefully poured over ice (1000 g). The resulting slurry was extracted with CH2Cl (3×250 ml) and the organic extracts were combined, dried over MgSO4 and filtered. The solvent was removed in a rotary evaporator and the yellow crystals thus obtained were recrystallized from 50% Et2O/hexane to yield pure 3-nitro-4-methoxy-benzenesulfonyl-chloride (161.3 g, 89% yield) as faintly yellow crystals.

Quelle