Réaction #75253

Équation de réaction

4-acetoxy-5-propoxy-1-pentanol tosylate

sodium iodide

→

crude title compound

4-Acetoxy-5-propoxy-1-iodopentane

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   FiltrationThe precipitated sodium tosylate is filtered off
2. 2
   AutreMost of the acetone is evaporated from the filtrate
3. 3
   workup.ADDITIONthe residue is treated with 300 ml
4. 4
   Lavagewashed with dilute sodium thiosulfate solution, water, and brine
5. 5
   Séchagedried over sodium sulfate
6. 6
   workup.DISTILLATIONThe solvent is distilled in vacuo

Mode opératoire

A solution of 4-acetoxy-5-propoxy-1-pentanol tosylate (61.5 g., 0.179 mole) and sodium iodide (79.5 g., 0.53 mole) in acetone (500 ml.) is allowed to stand at 25°-27° C. for 18 hours. The precipitated sodium tosylate is filtered off. Most of the acetone is evaporated from the filtrate and the residue is treated with 300 ml. of water. The oily product is taken up in ether, washed with dilute sodium thiosulfate solution, water, and brine, and dried over sodium sulfate. The solvent is distilled in vacuo to give a quantitative yield of the crude title compound as a yellowish oil which is used without further purification.

Source