m-Chloroperbenzoic acid → Diethyl(benzylsulfinylmethyl)phosphonate

HRID 372821Notes

Reaction equation

HRID 372821 reaction equation
[CH2:1]([S:8][CH2:9][P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[CH2:12]([O:11][P:10]([CH2:9][S:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:23])(=[O:17])[O:14][CH2:15][CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12536437Diethyl(benzylthiomethyl)phosphonate

Product 1

HCID 23420192Diethyl(benzylsulfinylmethyl)phosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of diethyl (benzylthiomethyl)phosphonate (10 g., 0.036 mole) in 75 ml. of methylene chloride was, with ice-bath cooling, treated with 7.29 g. (0.036 mole) of m-chloroperoxybenzoic acid portionwise. After the addition was complete, the mixture was stirred for 1 hour at ambient temperature, filtered to remove precipitate, and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel by eluting the column with ethyl acetate which gave 5.9 g. of the title compound.

Workup

  1. temperaturecooling
  2. additiontreated with 7.29 g
  3. additionAfter the addition
  4. filtrationfiltered
  5. customto remove precipitate
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was chromatographed on silica gel
  8. washby eluting the column with ethyl acetate which
  9. customgave 5.9 g

Sources & evidence

ORD record
ord-48b7b2d6cb9942ddb456fbc435822287
Source dataset
uspto-grants-1978_05
Patent number
US04092349

Reaction notes

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