Hydrochloric Acid → 3-Mercapto-4-methoxyphenylacetone

HRID 1614739Notes

Reaction equation

HRID 1614739 reaction equation
Cl.Cl[S:3]([C:6]1[CH:7]=[C:8]([CH2:14][C:15](=[O:17])[CH3:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13])(=O)=O>C(O)(=O)C.O>[SH:3][C:6]1[CH:7]=[C:8]([CH2:14][C:15](=[O:17])[CH3:16])[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 131062582-Methoxy-5-(2-oxopropyl)benzenesulfonyl chloride

Product 1

HCID 131788863-Mercapto-4-methoxyphenylacetoneYield 93.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

While ice-cooling a suspension of 84 g of stannous chloride-2H2O in 320 ml of glacial acetic acid with stirring until a transparent solution was obtained, hydrochloric acid gas was introduced into the solution and then 14.3 g of 3-chlorosulfonyl-4-methoxyphenylacetone was added to the solution at 25°-30° C. After further stirring the mixture at room temperature for 30 minutes, the reaction mixture obtained was poured into 320 ml of concentrated hydrochloric acid and after diluting the mixture with 640 ml of water, the product was extracted with 400 ml of chloroform. The chloroform layer formed was washed with water and then chloroform was distilled off to provide 10 g of oily 3-mercapto-4-methoxyphenylacetone.

Workup

  1. temperatureWhile ice-cooling
  2. customwas obtained
  3. stirringAfter further stirring the mixture at room temperature for 30 minutes
  4. customthe reaction mixture obtained
  5. extractionthe product was extracted with 400 ml of chloroform
  6. customThe chloroform layer formed
  7. washwas washed with water
  8. distillationchloroform was distilled off

Sources & evidence

ORD record
ord-31e526a4f9314d45af1b420ba44be0e1
Source dataset
uspto-grants-1993_03
Patent number
US05198587

Reaction notes

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