4-Chlorobenzenesulfonyl chloride → Sodium 4-chlorobenzenesulfinate

HRID 247009Notes

Reaction equation

HRID 247009 reaction equation
S([O-])([O-])=O.[Na+:5].[Na+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([S:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[Na+:5]

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 24437Sodium Sulfite

Product 1

HCID 23664783Sodium 4-chlorobenzenesulfinateYield 1,009.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 504 g of sodium sulfite and 1.8 l of water was added portionwise 16 g of p-chlorobenzenesulfonyl chloride at 50° C. After being stirred at 55°-60° C. for 3 hours, the mixture was cooled with ice and white crystals which separated out were collected and washed with cold water to obtain 152 g of sodium p-chlorobenzenesulfinate. In a manner similar to Synthesis Example 1, sodium p-chlorobenzenesulfinate and ethyl chloroacetate were reacted to obtain ethyl p-chlorophenylsulfonyl acetate. The ester thus obtained (110 g) was added portionwise to a 20% sodium hydroxide aqueous solution while cooling with ice. During this procedure, white crystals separated out quickly. After stirring at room temperature for 1 hour, the mixture was cooled with ice and white crystals were collected by filtration and washed with isopropanol. The crystals thus obtained were dissolved in 300 ml of water and the solution was neutralized with diluted hydrochloric acid. The white crystals which separated out were collected by filtration, washed with water to obtain 90 g of p-chlorophenylsulfonylacetic acid.

Workup

  1. temperaturethe mixture was cooled with ice and white crystals which
  2. customseparated out
  3. customwere collected
  4. washwashed with cold water

Sources & evidence

ORD record
ord-5633748f20d0436b9223e1ee51e6f18b
Source dataset
uspto-grants-1987_11
Patent number
US04705737

Reaction notes

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