Hydrochloric Acid → 2-Methylbenzene-1-sulfinic acid

HRID 2227791Notes

Reaction equation

HRID 2227791 reaction equation
[Na+].[C:2]1([CH3:11])[C:3]([S:8]([O-:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.O.Cl>C(OC)(C)(C)C>[C:2]1([CH3:11])[C:3]([S:8]([OH:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 23676349o-Toluenesulfinic acid, sodium salt

Product 1

HCID 126612952-Methylbenzene-1-sulfinic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Toluenesulfinic acid sodium salt (150 g, 0.84 mol), H2O (500 mL), and t-butylmethyl ether (TBME) (250 mL) were vigorously stirred, and concd HCl (75 mL) was added dropwise. The resulting two phases were separated and the aqueous phase was extracted with TBME (100 mL). The TBME phases were dried (Na2SO4) and concentrated to near dryness and the white solid was combined with hexane (350 mL) and filtered and dried in vacuo to afford 96 g of toluenesulfinic acid.

Workup

  1. customThe resulting two phases were separated
  2. extractionthe aqueous phase was extracted with TBME (100 mL)
  3. dry with materialThe TBME phases were dried (Na2SO4)
  4. concentrationconcentrated
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d269452577b84616bcce07a769f69866
Source dataset
uspto-grants-2002_07
Patent number
US06414150B1

Reaction notes

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