m-Chloroperbenzoic acid → 3-Chlorobenzoic Acid

HRID 28211

Reaction equation

HRID 28211 reaction equation
OC1(CCN2C(=O)CSC2CCCC2C=CC(C(O)=O)=CC=2)CCCCC1.[Cl:28][C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32]([O:34]O)=[O:33]>C(Cl)(Cl)Cl>[Cl:28][C:29]1[CH:30]=[C:31]([CH:36]=[CH:37][CH:38]=1)[C:32]([OH:34])=[O:33]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1750274-(3-((2-(1-Hydroxycyclohexyl)ethyl)-4-oxo-2-thiazolidinyl)propyl)benzoic acid

Product 1

HCID 4473-Chlorobenzoic Acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 4-{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-375eefff29a44514bd40b491acd8f786
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Linked notes

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