Reacción #50780

Ecuación de reacción

2-chloroethanol

sodium hydroxide

hydrochloric acid

sodium hydroxide

4-hydroxy-3-methylmandelic acid

sodium hydroxide

2-chloroethanol

→

4-(2-hydroxyethoxy)-3-methylmandelic acid

Disolventes

water

water

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ethyl acetate
2. 2
   LavadoThe organic phases are washed with water
3. 3
   Secadodried over magnesium sulfate
4. 4
   Concentraciónconcentrated on a vacuum rotary evaporator

Procedimiento

A solution of 8.0 g (200 mmol) of sodium hydroxide in 15 ml of water is added dropwise over a period of one hour to a solution of 18.2 g (100 mmol) of 4-hydroxy-3-methylmandelic acid (Example 13), 4.0 g (100 mmol) of sodium hydroxide and 13.4 ml (200 mmol) of 2-chloroethanol in 60 ml water heated to 70° C. Another 6.7 ml (100 mmol) of 2-chloroethanol and 4.0 g (100 mmol) of sodium hydroxide in 10 ml of water are then added. After another 15 minutes, the reaction mixture is acidified with concentrated hydrochloric acid and extracted twice with ethyl acetate. The organic phases are washed with water, combined, dried over magnesium sulfate and concentrated on a vacuum rotary evaporator. This gives 23.0 g (about 100%) of 4-(2-hydroxyethoxy)-3-methylmandelic acid as a yellowish resin (compound (203), Table 2).

Fuente