Chloroform → alpha-Chloro-3-nitrobenzaldoxime
Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[CH:7]=[N:8][OH:9])([O-:3])=[O:2].C(Cl)(Cl)[Cl:14]>>[Cl:14][C:7](=[N:8][OH:9])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1Participants
3
Procedure
32.9 g (0.2 mol) of 3-nitrobenzaldoxime was suspended in 150 g of chloroform and chlorine gas was bubbled into the suspension while maintaining the reaction mixture at a temperature of from 5° to 10°C. 3-Nitrobenzaldoxime went into solution showing a green color upon reaction with chlorine to give a reaction mixture having a deep green color. The reaction mixture turned a pale yellowish-brown upon standing; chloroform was then removed from the reaction mixture under reduced pressure to give 37.6 g of pale yellow crystals having a melting point of 98°-101°C. Yield, 94%.
Workup
- customchlorine gas was bubbled into the suspension
- temperaturewhile maintaining the reaction mixture at a temperature of from 5° to 10°C