Reacción #69342

Ecuación de reacción

p-toluenesulfonyl chloride

ethylene glycol monomethyl ether

→

Toluene-4-sulfonic acid 2-methoxy-ethyl ester

Disolventes

pyridine

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Extracciónis extracted with dichloromethane (1.2 l)
3. 3
   LavadoThe organic layer is washed with ice-cold 6 M HCl (3×350 ml)
4. 4
   Otrois reduced to a minimum volume by evaporation in vacuo

Procedimiento

A slurry of p-toluenesulfonyl chloride (205 g, 1.08 mol) and pyridine (150 mL) is stirred under an argon atmosphere. The temperature is maintained below 5° C. (ice-water bath), while ethylene glycol monomethyl ether (80 ml, 1 mol) is added slowly from a dropping funnel. After the addition is complete, the mixture is stirred for 1 h below 5° C. The mixture is poured into ice-water (1 L) and is extracted with dichloromethane (1.2 l). The organic layer is washed with ice-cold 6 M HCl (3×350 ml), and is reduced to a minimum volume by evaporation in vacuo.

Fuente