Water → Benzoic acid, 3-sulfo-

HRID 273914

Reaction equation

HRID 273914 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].O>C1(C)C(C)=CC=CC=1>[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])([OH:16])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 144744642-(Chlorosulfonyl)benzoic acid

Product 1

HCID 8477Benzoic acid, 3-sulfo-Yield 95.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
100 °C

Procedure

300 g of 3-(chlorosulfonyl)benzoic acid containing 38.8% water (corresponding to 183.6 g (0.83 mol) of 100% chlorosulfonylbenzoic acid) are admixed with 150 g of water and heated at 100° C. for 1 hour. Then 600 g of xylene are added dropwise over 1 hour and a total of 260 ml of water are azeotropically distilled off with xylene. The reaction mixture is cooled and the precipitate is filtered off with suction. After drying at 100° C./100 torr (13.16 kPa) 164.7 g of 3-sulfobenzoic acid are obtained, the purity determined by titration being 97.7%; this corresponds to a yield of 95.6%.

Workup

  1. distillationa total of 260 ml of water are azeotropically distilled off with xylene
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe precipitate is filtered off with suction
  4. dry with materialAfter drying at 100° C./100 torr (13.16 kPa) 164.7 g of 3-sulfobenzoic acid
  5. customare obtained

Sources & evidence

ORD record
ord-5c21ac4fce2b41ce973bccab5db1a867
Source dataset
uspto-grants-1995_02
Patent number
US05387711

Linked notes

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