m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 443671Notes

Reaction equation

HRID 443671 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 acid

Product 1

HCID 4473-Chlorobenzoic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 4-{-b 3-[3-[2-(1-hydroxycyclohexyl)-ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid (0.391 g., 1.0 mmol.), m-chloroperoxybenzoic acid (100%, 0.362 g., 2.1 mmol.), and chloroform (5 ml.) is refluxed for 30 minutes. The reaction mixture is evaporated in vacuo to give a solid residue which is applied to a silica gel column (18 g.) with chloroform. Elution with chloroform-acetic acid (25:1; v:v; 150 ml.) provides m-chlorobenzoic acid and impure material. Continued elution with the same eluant affords the title compound as a colorless viscous oil (0.273 g., 0.64 mmol., 64%), pmr (CDCl3) δ 3.75 (2H, s), 4.60 (1H, m), 7.26 (2H, d), 8.00 (2H, d).

Workup

  1. temperatureis refluxed for 30 minutes
  2. customThe reaction mixture is evaporated in vacuo
  3. customto give a solid residue which
  4. washElution with chloroform-acetic acid (25:1; v:v; 150 ml.)

Sources & evidence

ORD record
ord-880a572f8918460db63a6178888c5f5b
Source dataset
uspto-grants-1981_04
Patent number
US04260771

Reaction notes

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