m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 542083Notes

Reaction equation

HRID 542083 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10]O)=[O:9])[CH:3]=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 4473-Chlorobenzoic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Compounds of Formula Ib wherein R4 =R9SO can be prepared from the appropriate compounds of Formula Ia wherein R4 =R9S by oxidation with m-chloroperbenzoic acid as shown in Equation 10. The reaction can be carried out by stirring equivalent amounts of Ia with m-chloroperbenzoic acid (MCPBA) in an inert solvent such as chloroform at 0° to reflux for 12-24 hours. The insoluble m-chlorobenzoic acid produced is removed by filtration and the chloroform solution is concentrated to yield the crude product. Purification by standard techniques will give the desired product. Oxidation of Ia with one equivalent of hydrogen peroxide in acetic acid at room temperature will also give the sulfoxides Ib. ##STR24##

Workup

  1. customThe reaction
  2. temperatureto reflux for 12-24 hours

Sources & evidence

ORD record
ord-fe9ece4716904e4f91e6fe2c3b2d7749
Source dataset
uspto-grants-1987_04
Patent number
US04655822

Reaction notes

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