Reaction #56489

Reaction equation

4-{3-[3-[2-(1-hydroxycyclohexyl)ethyl]-4-oxo-2-thiazolidinyl]propyl}benzoic acid

m-chloroperoxybenzoic acid

→

m-chlorobenzoic acid

Solvents

chloroform

chloroform

Conditions

Workup

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

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).

Source