Hydrochloric Acid → p-Toluenesulfinic acid

HRID 2394802Notes

Reaction equation

HRID 2394802 reaction equation
[Na+].[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(OC)(C)(C)C.Cl>O>[C:2]1([CH3:11])[CH:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 15413tert-Butyl methyl etherHCID 2723791Sodium p-toluenesulfinate

Product 1

HCID 10818p-Toluenesulfinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of p-toluenesulfinic acid sodium salt (30 g) in H2O (100 mL) was added methyl t-butyl ether (50 mL) followed by dropwise addition of conc HCl (15 mL). After stirring 5 min, the organic phase was removed and the aqueous phase was extracted with methyl t-butyl ether. The organic phase was dried (Na2SO4) and concentrated to near dryness. Hexane was added and the resulting precipitate collected to afford p-toluenesulfinic acid; yield 22 g.

Workup

  1. customthe organic phase was removed
  2. extractionthe aqueous phase was extracted with methyl t-butyl ether
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated
  5. additionHexane was added
  6. customthe resulting precipitate collected

Sources & evidence

ORD record
ord-19b2517dc53f4b7b8d1046e8ec75c639
Source dataset
uspto-grants-1998_09
Patent number
US05811549

Reaction notes

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