Sodium Sulfite → Sodium (4-nitrophenyl)methanesulfonate

HRID 1463325Notes

Reaction equation

HRID 1463325 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[S:12]([O-:15])([O-:14])=[O:13].[Na+:16].[Na+]>CO.O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][S:12]([O-:15])(=[O:14])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Na+:16]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 660114-Nitrobenzyl bromide

Product 1

HCID 5314401Sodium (4-nitrophenyl)methanesulfonateYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 100g (463 mmol, 1.0 equiv.) of 4-nitrobenzyl bromide and 64.2 g (509 mmol, 1.1 equiv.) of sodium sulfite in 500 mL of methanol and 500 mL of water was heated to reflux. The progress of the reaction was monitored by TLC. When the bromide was consumed, the reaction mixture was allowed to cool to room temperature. The product precipitated and was collected by filtration. It was thoroughly dried for sixteen hours at 65° C. at 0.05 mm Hg to give 100 g (90%) of sodium 4-nitrobenzyl sulfonate.

Workup

  1. temperaturewas heated to reflux
  2. customWhen the bromide was consumed
  3. customThe product precipitated
  4. filtrationwas collected by filtration
  5. customIt was thoroughly dried for sixteen hours at 65° C. at 0.05 mm Hg

Sources & evidence

ORD record
ord-27e8d494efc44475a829d253558a0245
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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