Nitric Acid → Benzenesulfonyl chloride, 4-methoxy-3-nitro-

HRID 1731727Notes

Reaction equation

HRID 1731727 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([Cl:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1>>[N+:1]([C:12]1[CH:11]=[C:10]([S:13]([Cl:16])(=[O:14])=[O:15])[CH:9]=[CH:8][C:7]=1[O:6][CH3:5])([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric Acid2×HCID 74014-Methoxybenzenesulfonyl chloride

Product 1

HCID 89600Benzenesulfonyl chloride, 4-methoxy-3-nitro-Yield 89%

Procedure

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.

Workup

  1. temperatureTo maintain control
  2. customover the very vigorous reaction which
  3. customto react completely (i.e.
  4. additionwas added
  5. additionWhen addition
  6. extractionThe resulting slurry was extracted with CH2Cl (3×250 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed in a rotary evaporator
  10. customthe yellow crystals thus obtained
  11. customwere recrystallized from 50% Et2O/hexane

Sources & evidence

ORD record
ord-eeb3ed0e12a04ecfa423af82895245da
Source dataset
uspto-grants-1986_11
Patent number
US04623484

Reaction notes

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