Reacción #80925

Ecuación de reacción

water

2,6-dichlorobenzonitrile

2-methyl-2-propen-1-ol

potassium hydroxide

→

2-methyl-3-(3-chloro-2-cyanophenoxy)-1-propene

Rendimiento 93.8%

Disolventes

dimethyl sulfoxide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONDuring the addition
2. 2
   Otrorose from 20° C. to about 35° C
3. 3
   workup.ADDITIONUpon completion of the addition
4. 4
   FiltraciónThe mixture was filtered
5. 5
   Otroto collect a solid
6. 6
   LavadoThe solid was washed with water
7. 7
   Otrodried under vacuum

Procedimiento

A solution of 30.0 grams (0.174 mole) of 2,6-dichlorobenzonitrile and 14.7 mL (0.174 mole) of 2-methyl-2-propen-1-ol in 200 mL of dimethyl sulfoxide was stirred, and 12.7 grams (0.191 mole) of 85% potassium hydroxide was added portionwise during a 5 minute period. During the addition, the reaction mixture temperature rose from 20° C. to about 35° C. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into 600 mL of water. The mixture was filtered to collect a solid. The solid was washed with water and dried under vacuum, yielding 33.9 grams of 2-methyl-3-(3-chloro-2-cyanophenoxy)-1-propene. The NMR spectrum was consistent with the proposed structure.

Fuente