m-Chloroperbenzoic acid → HCID 19022416, compound

HRID 1109322Notes

Reaction equation

HRID 1109322 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-20005c5eebe741b2897f5f2306bb0281
Source dataset
uspto-grants-1994_06
Patent number
US05319140

Reaction notes

Loading…