Reaktion #172302

Reaktionsgleichung

p-toluenesulfonyl chloride

2-chloroethanol

→

2-chloroethyl 4-methylbenzenesulfonate

Ausbeute 88.4%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate (3×100 mL)
2. 2
   WaschenThe combined organic layers were washed with 1 N HCl (3×100 mL), water (100 mL×3)
3. 3
   Trocknendried (Na2SO4)
4. 4
   Einengenconcentrated under reduced pressure

Vorschrift

In a typical run, p-toluenesulfonyl chloride (TsCl, 70.5 g, 0.37 mol) was added slowly to a solution of 2-chloroethanol (38; 25.0 g, 0.31 mol) in pyridine (100 mL) at 0° C. The reaction mixture was stirred at 0-5° C. for 18 h. Ice water (300 mL) was added and the resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with 1 N HCl (3×100 mL), water (100 mL×3), dried (Na2SO4) and concentrated under reduced pressure to afford 2-chloroethyl 4-methylbenzenesulfonate 39 (64.3 g, 88%).

Quelle