Sodium Hydroxide → Benzoic acid, 3-sulfo-, sodium salt (1:1)

HRID 273917Notes

Reaction equation

HRID 273917 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].ClS(C1C=CC=CC=1C(O)=O)(=O)=[O:16].[OH-].[Na+:28]>O.ClC1C=CC=CC=1>[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O-:10])=[O:9])([OH:16])(=[O:4])=[O:3].[Na+:28]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 144744642-(Chlorosulfonyl)benzoic acid

Product 1

HCID 23668512Benzoic acid, 3-sulfo-, sodium salt (1:1)Yield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent4×HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
100 °C

Procedure

273.6 g of 3-(chlorosulfonyl)benzoic acid containing 28.6% water (corresponding to 195.3 g (0.89 mol) of 100% chlorosulfonylbenzoic acid) are admixed with 50 g of water and 500 g of chlorobenzene and heated in a water separator. A total of 106 ml of water are expelled. After cooling the reaction mixture to 100° C., 108 g (0.89 mol) of 33% strength sodium hydroxide solution are added dropwise over 30 minutes. Subsequently a further 90 ml of water are expelled. After cooling, the precipitated product is filtered off with suction. After drying at 100° C./100 torr (13.16 kPa) 190.4 g of sodium 3-sulfobenzoate are obtained, the purity determined by titration being 97.3%; this corresponds to a yield of 93.3%.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated product is filtered off with suction
  3. dry with materialAfter drying at 100° C./100 torr (13.16 kPa) 190.4 g of sodium 3-sulfobenzoate
  4. customare obtained

Sources & evidence

ORD record
ord-c6457796433540e39b6aa2d2a4fe5655
Source dataset
uspto-grants-1995_02
Patent number
US05387711

Reaction notes

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