O-Xylene → Benzoic acid, 3-sulfo-

HRID 273916

Reaction equation

HRID 273916 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].C1(C)C(C)=CC=CC=1>O>[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 7237O-XyleneHCID 77641Benzoic acid, 3-(chlorosulfonyl)-HCID 144744642-(Chlorosulfonyl)benzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

250 g of 3-(chlorosulfonyl)benzoic acid containing 35.9% of water (corresponding to 160.2 g (0.73 mol) of 100% chlorosulfonylbenzoic acid) are admixed with 86 g of water and 500 g of xylene and heated in a water separator. A total of 171 ml of water are expelled. The reaction mixture is cooled and the precipitated product filtered off with suction. After drying at 100° C./100 torr (13.16 kPa) 144.3 g of 3-sulfobenzoic acid are obtained, the purity determined by titration being 97.5%; this corresponds to a yield of 95.6%.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationthe precipitated product filtered off with suction
  3. dry with materialAfter drying at 100° C./100 torr (13.16 kPa) 144.3 g of 3-sulfobenzoic acid
  4. customare obtained

Sources & evidence

ORD record
ord-ea9334db84a745cb83f4e6db1939604c
Source dataset
uspto-grants-1995_02
Patent number
US05387711

Linked notes

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