Hydrochloric Acid → 2-Chloro-5-sulfino-benzoic acid

HRID 736131

Reaction equation

HRID 736131 reaction equation
S([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:16]=[CH:15][C:14]([S:17](F)(=[O:19])=[O:18])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[OH-].[Na+].Cl>O>[Cl:7][C:8]1[CH:16]=[CH:15][C:14]([S:17]([OH:19])=[O:18])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 888732-Chloro-5-(fluorosulpho)benzoic acid

Product 1

HCID 151129042-Chloro-5-sulfino-benzoic acidYield 76.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 33.59 g (267 mmol) sodium sulfite in 100 ml water at 0° C. is treated with 21.2 g (89 mmol) 2-Chloro-5-fluorosulfonyl-benzoic acid and 26.6 ml of a 10M aqueous NaOH solution (267 mmol). The mixture was allowed to stir for 3 h at room temperature, acidified with HCl conc. (pH=4) and water was removed under vacuum. Methanol was added, the precipitate filtered off and the filtrate concentrated. Methanol and diethylether were added and the precipitate was filtered off washed with ether and dried to yield 15 g (76.5%) of the title compound as white gum. MS (m/e): 219.1 (MH−, 100%)

Workup

  1. customwas removed under vacuum
  2. additionMethanol was added
  3. filtrationthe precipitate filtered off
  4. concentrationthe filtrate concentrated
  5. additionMethanol and diethylether were added
  6. filtrationthe precipitate was filtered off
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-958937b71f684eb692686f567009c3c3
Source dataset
uspto-grants-2009_09
Patent number
US07595314B2

Linked notes

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