m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 370612Notes

Reaction equation

HRID 370612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7]O)=[O:6]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([OH:7])=[O:6]

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, where R=SOCH(R2)A can be prepared from the appropriate compounds of Formula Ia wherein R=SCH(R2)A by oxidation with m-chloroperoxybenzoic acid as shown in Equation 12. The reaction can be carried out by stirring equivalent amounts of Ia with m-chloroperoxybenzoic 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. ##STR35##

Workup

  1. customCompounds of Formula Ib, where R=SOCH(R2)A can be prepared from the appropriate compounds of Formula Ia wherein R=
  2. customThe reaction
  3. temperatureto reflux for 12-24 hours

Sources & evidence

ORD record
ord-a5e2917e35204dc09975cd1988f5f766
Source dataset
uspto-grants-1985_07
Patent number
US04528024

Reaction notes

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