Sulfuric Acid → HCID 22118382, compound

HRID 1275451Notes

Reaction equation

HRID 1275451 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH3:11])=[CH:8][C:7]([S:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15]([OH:17])=O)=[C:6]([Cl:20])[CH:5]=1)([OH:3])=[O:2].S(=O)(=O)(O)O>ClCCl>[C:1]([C:4]1[C:9]([O:10][CH3:11])=[C:8]2[C:7](=[C:6]([Cl:20])[CH:5]=1)[S:12][CH2:13][C:14]([CH3:19])([CH3:18])[C:15]2=[O:17])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22118455HCID 22118455, compound

Product 1

HCID 22118382HCID 22118382, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

19.9 Grams (62 mmol) of 3-(4-carboxy-2-chloro-5-methoxyphenylthio)pivalic acid was dissolved in 400 ml of dichloromethane, and while the reaction temperature was maintained below 5° C. with ice bath cooling, 16.9 ml (corresponding to 81 mmol of SO3) of 20 wt % fuming sulfuric acid was gradually added. The reaction mixture was stirred at the same temperature for 30 minutes, then the ice bath was removed and stirred for 1 hour. Ice water was added to the reaction mixture to wash an organic layer, and then the organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 15.6 g (yield 83%) of the titled compound.

Workup

  1. temperaturewhile the reaction temperature was maintained below 5° C. with ice bath
  2. temperaturecooling
  3. customthe ice bath was removed
  4. stirringstirred for 1 hour
  5. additionIce water was added to the reaction mixture
  6. washto wash an organic layer
  7. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-70c476bedf534250b2ddc60bf0ab9a43
Source dataset
uspto-grants-2000_12
Patent number
US06159904

Reaction notes

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