Réaction #2146707

Équation de réaction

potassium iodide

p-toluenesulfonyl chloride

1,3-propanediol

→

1,3-propanediol mono-p-toluenesulfonate

Rendement 53.5%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   FiltrationInsoluble matters were filtered out of the reaction mixture
2. 2
   Lavagewere washed with ethyl acetate
3. 3
   Concentrationthe mixture was concentrated
4. 4
   AutreThe resulting crude product was purified with flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2 to 1/1)

Mode opératoire

1.45 mL (corresponding to 20.0 mmol) of 1,3-propanediol was dissolved in 200 mL of methylene chloride. To this solution under an ice bath, 6.96 g (corresponding to 30.0 mmol) of silver oxide, 666 mg (corresponding to 4.0 mmol) of potassium iodide and 4.21 g (corresponding to 22.0 mmol) of p-toluenesulfonyl chloride were added. The resulting mixture was stirred at room temperature for 3 hours. Insoluble matters were filtered out of the reaction mixture, and were washed with ethyl acetate. The washings were combined with the filtrate, and the mixture was concentrated. The resulting crude product was purified with flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2 to 1/1) to obtain 2.47 g (corresponding to 10.7 mmol) of 1,3-propanediol mono-p-toluenesulfonate (FIG. 1, Step 6).

Source