Sodium Sulfite → Sodium 2-chlorobenzene-1-sulfinate

HRID 1944446Notes

Reaction equation

HRID 1944446 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].O1CCOCC1.C(=O)(O)[O-].[Na+:22].S([O-])([O-])=O.[Na+].[Na+]>O>[Na+:22].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 312751,4-DioxaneHCID 761872-Chlorobenzenesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 23719078Sodium 2-chlorobenzene-1-sulfinateYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2-chlorobenzenesulfonyl chloride (2.5 g) and dioxane (35 mL) was treated with a mixture of sodium bicarbonate (2.0 g), sodium sulfite (3.0 g) and water (17 mL), and the resulting mixture was heated at 75° C. for 30 minutes. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was triturated with ethanol, filtered and the filtrate concentrated under reduced pressure. The residue was triturated with acetonitrile to afford the title compound as a white solid (2.3 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with ethanol
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was triturated with acetonitrile

Sources & evidence

ORD record
ord-ce1e75f48d66433b9b338dc893c648cd
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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