m-Chloroperbenzoic acid → 1-(2-Chloroethanesulfinyl)heptane

HRID 2226471Notes

Reaction equation

HRID 2226471 reaction equation
[CH2:1]([S:8][CH2:9][CH2:10][Cl:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].ClC1C=CC=C(C(OO)=[O:20])C=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([S:8]([CH2:9][CH2:10][Cl:11])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 304371NSC196182HCID 516892Sodium BicarbonateHCID 656671Sodium Pyrosulfite

Product 1

HCID 3043751-(2-Chloroethanesulfinyl)heptaneYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Dissolve 2-chloroethyl heptyl sulfide (1.0 g, 5.13 mmol) in methylene chloride (50 mL), cool to -20° C. and place under nitrogen atmosphere. Add, by dropwise addition, a solution of meta-chlorperbenzoic acid (1.25 g, 6.0 mmol) in methylene chloride. Stir at -20° C. for 3 hours, then allow to warm to room temperature. Treat with saturated sodium meta bisulfite (until negative starch-iodide test) and basify with saturated sodium hydrogen carbonate. Extract with methylene chloride (2×25 mL), dry (MgSO4) and evaporate in vacuo to yield 1.2 g of 2chloroethyl heptyl sulfoxide as white crystals; MS (CI/CH4) m/z 211(M+1).

Workup

  1. additionAdd, by dropwise addition
  2. temperatureto warm to room temperature
  3. extractionExtract with methylene chloride (2×25 mL)
  4. dry with materialdry (MgSO4)
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-3c2c937d1f2f4d95872e7a88d37dee74
Source dataset
uspto-grants-1994_09
Patent number
US05348964

Reaction notes

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