m-Chloroperbenzoic acid → HCID 54013640, compound

HRID 363080Notes

Reaction equation

HRID 363080 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([Cl:19])=[CH:17][C:16]([O:20][CH2:21][CH:22]=[C:23]([Cl:25])[Cl:24])=[CH:15][C:14]=2[Cl:26])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([Cl:19])=[CH:17][C:16]([O:20][CH2:21][CH:22]=[C:23]([Cl:24])[Cl:25])=[CH:15][C:14]=2[Cl:26])=[O:35])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54339509HCID 54339509, compound

Product 1

HCID 54013640HCID 54013640, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.50 g of 1-(3-(4-chlorophenylthio)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene and 20 ml of methylene chloride was stirred under cooling with ice-water, to which 0.26 g of m-chloroperbenzoic acid was added. After stirring at room temperature for 24 hours, the methylene chloride layer was separated, washed successively with saturated aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated saline solution, dried with magnesium sulfate, and concentrated to obtain a crude product. The crude product was subjected to silica gel chromatography, which afforded 0.38 g of 1-(3-(4-chlorophenylsulfinyl)propyloxy)-2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)benzene (73% yield), nD24.5 1.5962.

Workup

  1. additionwas added
  2. stirringAfter stirring at room temperature for 24 hours
  3. customthe methylene chloride layer was separated
  4. washwashed successively with saturated aqueous sodium sulfite solution, saturated aqueous sodium hydrogencarbonate solution and saturated saline solution
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. customto obtain a crude product

Sources & evidence

ORD record
ord-09b0008af391437e9944735423053a12
Source dataset
uspto-grants-1999_02
Patent number
US05872137

Reaction notes

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