m-Chloroperbenzoic acid → HCID 18965263, compound

HRID 2226467Notes

Reaction equation

HRID 2226467 reaction equation
C(S[CH2:7][CH2:8][CH2:9][Cl:10])CC(C)C.ClC1C=[CH:16][CH:15]=[C:14]([C:18](OO)=O)[CH:13]=1.[S:22](S([O-])=O)([O-:25])(=O)=[O:23].[Na+].[Na+]>C(Cl)Cl>[CH2:16]([S:22]([CH2:7][CH2:8][CH2:9][Cl:10])(=[O:25])=[O:23])[CH2:15][CH:14]([CH3:13])[CH3:18]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 656671Sodium PyrosulfiteHCID 18965257HCID 18965257, compound

Product 1

HCID 18965263HCID 18965263, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dissolve 3-chloropropyl isopentyl sulfide (800 mg, 4.43 mmol) in methylene chloride (25 mL) and place under nitrogen atmosphere. Add a solution of metachloroperbenzoic acid (1.53 g, 8.85 mmol) in methylene chloride (25 mL). Stir at room temperature overnight. Add additional meta-chloroperbenzoic acid (1.0 g) in methylene chloride (25 mL). Stir at room temperature overnight. Treat with aqueous sodium metabisulfite (until negative starch-iodide test) and separate the layers. Wash the organic phase with saturated sodium hydrogen carbonate until basic and dry (MgSO4). Evaporate the solvent in vacuo to yield 710 mg (75.4%) of 3-chloropropyl isopentyl sulfone as a yellow oil which crystallizes; MS (CI/CH4) m/z 213(M+1), 177(M+1-HCl).

Workup

  1. stirringStir at room temperature overnight
  2. customseparate the layers
  3. washWash the organic phase with saturated sodium hydrogen carbonate until basic and
  4. dry with materialdry (MgSO4)
  5. customEvaporate the solvent in vacuo

Sources & evidence

ORD record
ord-5f82486319cf4a1fbdc3d7c2becbe573
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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