m-Chloroperbenzoic acid → Ethyl phytyl sulfoxide

HRID 2254657Notes

Reaction equation

HRID 2254657 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:32][CH2:33][CH3:34])/[CH:13]=[C:14](/[CH2:16][CH2:17][CH2:18][C@@H:19]([CH2:21][CH2:22][CH2:23][C@@H:24]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:25])[CH3:20])\[CH3:15]>C(Cl)Cl>[CH2:12]([S:32]([CH2:33][CH3:34])=[O:9])/[CH:13]=[C:14](/[CH2:16][CH2:17][CH2:18][C@@H:19]([CH2:21][CH2:22][CH2:23][C@@H:24]([CH2:26][CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH3:25])[CH3:20])\[CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 131718073Ethyl phytyl thioether

Product 1

HCID 131718074Ethyl phytyl sulfoxideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.1 g of m-chloroperbenzoic acid was added to a solution of 10.0 g of ethyl phytyl thioether dissolved in 30 ml of methylene chloride. The resulting mixture was stirred for 2 hours at room temperature. After the completion of the reaction, the reaction mixture was washed with 2% aqueous sodium hdyrogensulfite solution, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: n-hexane:ethyl acetate =9:1) to obtain 9.4 g (yield: 90%) of oily ethyl phytyl sulfoxide.

Workup

  1. customAfter the completion of the reaction
  2. washthe reaction mixture was washed with 2% aqueous sodium hdyrogensulfite solution, 3% aqueous sodium hydrogencarbonate solution and water in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe residue obtained
  6. customwas purified by a column chromatography (eluant: n-hexane:ethyl acetate =9:1)

Sources & evidence

ORD record
ord-ea09e8afaffc4bc489bea6d2a548ee9f
Source dataset
uspto-grants-1993_08
Patent number
US05236950

Reaction notes

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