Sodium Sulfite → Sodium (4-nitrophenyl)methanesulfonate

HRID 1647776Notes

Reaction equation

HRID 1647776 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-8b39bbce930b423c8d549294b6187003
Source dataset
uspto-grants-1995_07
Patent number
US05434154

Reaction notes

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