Water → Benzoic acid, 3-sulfo-

HRID 273915

Reaction equation

HRID 273915 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].O.ClS(C1C=CC=CC=1C(O)=O)(=O)=[O:17]>C1(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:17])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962Water2×HCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 144744642-(Chlorosulfonyl)benzoic acid

Product 1

HCID 8477Benzoic acid, 3-sulfo-Yield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

300 g of 3-(chlorosulfonyl)benzoic acid containing 38.8% of water (corresponding to 183.6 g (0.83 mol) of 100% chlorosulfonylbenzoic acid) are admixed with 100 g of water and heated to 100° C. for 1 hour. Then 500 g of toluene are added dropwise over 1 hour and a total of 164 ml of water distilled off azeotropically with toluene. The reaction mixture is cooled and the precipitated product filtered off with suction. After drying at 100° C./100 torr (13.16 kPa) 163.5 g of 3-sulfobenzoic acid are obtained, the purity determined by titration being 98.2%; this corresponds to a yield of 95.4%.

Workup

  1. distillationa total of 164 ml of water distilled off azeotropically with toluene
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe precipitated product filtered off with suction
  4. dry with materialAfter drying at 100° C./100 torr (13.16 kPa) 163.5 g of 3-sulfobenzoic acid
  5. customare obtained

Sources & evidence

ORD record
ord-f331762fe48d4032a45a6428d40a8c32
Source dataset
uspto-grants-1995_02
Patent number
US05387711

Linked notes

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