Sulfuric Acid → HCID 21476989, compound

HRID 2293550Notes

Reaction equation

HRID 2293550 reaction equation
S(=O)(=O)(O)O.Cl[S:7]([C:10]1[C:11]([O:21][CH3:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16])(=O)=O>C(OCC)(=O)C.[Zn]>[CH3:20][O:19][C:13]1[CH:12]=[C:11]([O:21][CH3:22])[C:10]([SH:7])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 167713625-Chlorosulfonyl-2,4-dimethoxybenzoic acid

Product 1

HCID 21476989HCID 21476989, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To 20 g of crushed ice were added 3.7 ml of concentrated sulfuric acid and 1.90 g of 5-chlorosulfonyl-2,4-dimethoxybenzoic acid. Under ice-cooling, 2.40 g of zinc powder was added, and the mixture was then heated under reflux. After completion of the reaction, the reaction solution was diluted with ethyl acetate and insoluble matter was removed by celite filtration. The thus obtained filtrate was extracted with ethyl acetate, washed with water and saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure and the resulting residue was washed with diethyl ether to give 0.74 g of 2,4-dimethoxy-5-mercaptobenzoic acid.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturethe mixture was then heated
  3. temperatureunder reflux
  4. customAfter completion of the reaction
  5. customwas removed by celite filtration
  6. extractionThe thus obtained filtrate was extracted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under a reduced pressure
  10. washthe resulting residue was washed with diethyl ether

Sources & evidence

ORD record
ord-2fba43b7497741dba64a86001ce1a5a6
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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