2,3-Dimethoxybenzoic acid → 5-(Chlorosulfonyl)-2,3-dimethoxybenzoic acid

HRID 1388900Notes

Reaction equation

HRID 1388900 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]>O>[Cl:1][S:2]([C:14]1[CH:15]=[C:16]([O:17][CH3:18])[C:8]([O:7][CH3:6])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:5])=[O:3]

Participants

4

Reactant 2

HCID 152042,3-Dimethoxybenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 30185285-(Chlorosulfonyl)-2,3-dimethoxybenzoic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution, cooled to -5° C., of 511.7 g (200 ml) of chlorosulfonic acid (ClSO3H) are slowly added 80 g of 2,3-dimethoxy benzoic acid. Then the temperature is allowed to rise to 15° C., the mixture is poured into a solution of water and ice, and the precipitate formed is filtered. Thus, 100 g (yield: 80%) of 5-chlorosulfonyl 2,3-dimethoxy benzoic acid are obtained [(IIb), Melting point: 157° C⟧

Workup

  1. customto rise to 15° C.
  2. customthe precipitate formed
  3. filtrationis filtered

Sources & evidence

ORD record
ord-63604e198f3344e5be8bbd4700af8d39
Source dataset
uspto-grants-1984_02
Patent number
US04434170

Reaction notes

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