Sodium Carbonate → [{2-(1,3-Benzodioxol-5-yl)ethyl}sulfinyl]propan-2-one

HRID 486926Notes

Reaction equation

HRID 486926 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12][CH2:13][C:14](=[O:16])[CH3:15])=[CH:9][C:4]=2[O:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:25])C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][S:12]([CH2:13][C:14](=[O:16])[CH3:15])=[O:25])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 22367134[{2-(1,3-Benzodioxol-5-yl)ethyl}thio]propan-2-one

Product 1

HCID 22367163[{2-(1,3-Benzodioxol-5-yl)ethyl}sulfinyl]propan-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

4 g of [{2-(1,3-benzodioxol-5-yl)ethyl}thio]-propan-2-one was dissolved in 70 ml of chloroform. 3.2 g of 90% m-chloroperbenzoic acid was added to the solution under cooling with ice/water. The mixture was stirred for 40 min. 150 ml of chloroform and an aqueous sodium carbonate solution were added to the reaction mixture. After separation of the layers thus formed, the chloroform layer was washed with water three times and dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was recrystallized from isopropyl ether to obtain 3.5 g of the intended compound in the form of colorless crystals.

Workup

  1. customAfter separation of the layers
  2. customthus formed
  3. washthe chloroform layer was washed with water three times
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-eb93e423481e44b18020c82efbc4772f
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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