Reaction #1960536

Reaction equation

potassium iodide

p-toluenesulfonylchloride

ethylene glycol

→

2-hydroxyethyl-p-toluenesulfonate

Yield 29.7%

Solvents

methylene chloride

Conditions

Workup

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

Procedure

621 mg (corresponding to 10.0 mmol) of ethylene glycol was dissolved in 100 mL of methylene chloride. To this solution under an ice bath, 3.49 g (corresponding to 15.0 mmol) of silver oxide, 350 mg (corresponding to 2.1 mmol) of potassium iodide and 2.10 g (corresponding to 11.0 mmol) of p-toluenesulfonylchloride were added. The resulting mixture was stirred at 0° C. for 2 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 by flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=1/1) to obtain 643 mg (corresponding to 2.97 mmol) of 2-hydroxyethyl-p-toluenesulfonate (FIG. 1-3, Step 3).

Source