m-Chloroperbenzoic acid → [{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}sulfinyl]acetic acid

HRID 486901Notes

Reaction equation

HRID 486901 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:14]([CH:22]([S:24][CH2:25][C:26]([OH:28])=[O:27])[CH3:23])=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1>C(Cl)(Cl)Cl>[CH3:12][C:13]1[C:14]([CH:22]([S:24]([CH2:25][C:26]([OH:28])=[O:27])=[O:9])[CH3:23])=[CH:15][C:16]2[O:20][CH2:19][O:18][C:17]=2[CH:21]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 14514909[{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}thio]acetic acid

Product 1

HCID 14514921[{1-(6-Methyl-1,3-benzodioxol-5-yl)ethyl}sulfinyl]acetic acidYield 11.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.7 g of 80% m-chloroperbenzoic acid was added to a solution of 2.0 g of [{1-(6-methyl-1,3-benzodioxol-5-yl)ethyl}thio]acetic acid in 40 ml of chloroform under cooling with ice. The mixture was stirred at room temperature overnight and a crystalline insoluble matter was recovered by filtration and washed with ether to obtain 0.24 g of the intended compound (as a single diastereomer) in the form of white crystals.

Workup

  1. temperatureunder cooling with ice
  2. filtrationa crystalline insoluble matter was recovered by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-b74c5103377141cc999166776f09d017
Source dataset
uspto-grants-1994_03
Patent number
US05292901

Reaction notes

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