Reaktion #80925

Reaktionsgleichung

water

2,6-dichlorobenzonitrile

2-methyl-2-propen-1-ol

potassium hydroxide

→

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

Ausbeute 93.8%

Lösungsmittel

dimethyl sulfoxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONDuring the addition
2. 2
   Sonstigerose from 20° C. to about 35° C
3. 3
   workup.ADDITIONUpon completion of the addition
4. 4
   FiltrationThe mixture was filtered
5. 5
   Sonstigeto collect a solid
6. 6
   WaschenThe solid was washed with water
7. 7
   Sonstigedried under vacuum

Vorschrift

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.

Quelle