m-Chloroperbenzoic acid → HCID 18965288, compound
Reaction equation
[CH2:1]([S:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])[CH2:2][CH:3]([CH3:5])[CH3:4].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[CH2:1]([S:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Cl:12])=[O:21])[CH2:2][CH:3]([CH3:5])[CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
Dissolve 5-chloropentyl isopentyl sulfide (1.0 g, 5.39 mmol) in methylene chloride (25 mL), place under nitrogen atmosphere and cool to -20° C. Add, by dropwise addition, a solution of meta-chloroperbenzoic acid (930 mg, 5.39 mmol) in methylene chloride (25 mL). Stir overnight at room temperature. Add additional meta-chloroperbenzoic acid (930 mg). Stir briefly and filter. 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 a yellow oil. Purify by silica gel chromatography (50% ethyl acetate/hexane) to yield 750 mg of 5-chloropentyl isopentyl sulfoxide as a clear oil; MS (CI/CH4) m/z 225(M+1), 189 (M+1-HCl).
Workup
- additionAdd, by dropwise addition
- stirringStir briefly
- filtrationfilter
- additionTreat with aqueous sodium metabisulfite (until negative starch-iodide test)
- customseparate the layers
- washWash the organic phase with saturated sodium hydrogen carbonate until basic and
- dry with materialdry (MgSO4)
- customEvaporate the solvent in vacuo
- customto yield a yellow oil
- customPurify by silica gel chromatography (50% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-ba7c86315e0f42ba9a12a20435446c2a
- Source dataset
- uspto-grants-1994_09
- Patent number
- US05348964
Reaction notes
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