m-Chloroperbenzoic acid → HCID 19022416, compound

HRID 1461053Notes

Reaction equation

HRID 1461053 reaction equation
[CH3:1][C:2]1([CH3:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([S:11][CH3:12])=[CH:10][C:4]=2[O:3]1.ClC1C=CC=C(C(OO)=[O:22])C=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([S:11]([CH3:12])=[O:22])=[CH:10][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 19022409HCID 19022409, compound

Product 1

HCID 19022416HCID 19022416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 19.6 g of 2,2-dimethyl-5-(methylthio)-1,3-benzodioxol in 500 ml of methylene chloride was treated at 0° C. with 20.3 g of 85% m-chloroperbenzoic acid. The mixture was subsequently stirred at 0° C. for 1 hour. A white precipitate resulted. The reaction mixture was extracted with 400 ml of 17% aqueous sodium carbonate solution and 400 ml of water. The organic phase was dried over sodium sulphate and freed from solvent in a vacuum. The residue was taken up in a small amount of methylene chloride and chromatographed on silica gel, with elution being carried out with ethyl acetate/n-hexane/methylene chloride (1:1:1, v/v/v). After crystallization from ethyl acetate/n-hexane, there was obtained 2,2-dimethyl-5-(methyl-sulphinyl)-1,3-benzodioxol as white crystals having a melting point of 87°-88° C.

Workup

  1. customA white precipitate resulted
  2. extractionThe reaction mixture was extracted with 400 ml of 17% aqueous sodium carbonate solution and 400 ml of water
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customchromatographed on silica gel, with elution
  5. customAfter crystallization from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-fe7cb8f519744032b2c6f03976e17eb9
Source dataset
uspto-grants-1991_12
Patent number
US05073550

Reaction notes

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