Sulfuric Acid → 2-Hydroxy-5-sulfinobenzoic acid

HRID 1820791Notes

Reaction equation

HRID 1820791 reaction equation
S([O-])([O-])=O.[Na+].[Na+].Cl[S:8]([C:11]1[CH:12]=[CH:13][C:14]([OH:20])=[C:15]([CH:19]=1)[C:16]([OH:18])=[O:17])(=[O:10])=[O:9].[OH-].[Na+].OS(O)(=O)=O>O.O1CCOCC1.C(OCC)(=O)C>[OH:20][C:14]1[CH:13]=[CH:12][C:11]([S:8]([OH:10])=[O:9])=[CH:19][C:15]=1[C:16]([OH:18])=[O:17]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 27772405-(Chlorosulfonyl)-2-hydroxybenzoic acid

Product 1

HCID 2489022-Hydroxy-5-sulfinobenzoic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To 317 mmol sodium sulfite in 200 ml water at RT was added dropwise over 30 min a solution of 42.3 mmol 5-chlorosulfonyl-2-hydroxy-benzoic acid in 80 ml dioxane and stirring continued for a further 30 min. 5 M aq NaOH was then added dropwise until the reaction mixture was pH 14, and the mixture was then allowed to stir at RT for a further 2 h. The mixture was then cooled to 0° C. and concentrated H2SO4 added until the reaction mixture was pH 1. Ethyl acetate was added, and the phases were separated. The organic phase was dried with Na2SO4. Evaporation in vacuo yielded the title compound.

Workup

  1. stirringto stir at RT for a further 2 h
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried with Na2SO4
  4. customEvaporation in vacuo

Sources & evidence

ORD record
ord-3fe43502f7fc4d3aae174ea70241d34d
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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