Diethyl Ether → Chloroisovaniline

Reaktionsgleichung

[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:5]([OH:6])[CH:4]=1.C(O[Cl:17])(C)(C)C.CCOCC>CC(O)=O>[Cl:17][C:4]1[C:5]([OH:6])=[C:7]([O:8][CH3:9])[CH:10]=[CH:11][C:3]=1[CH:2]=[O:1]

Komponenten

Versuchsvorschrift

41.2 g (0.271 mol) of isovanillin was dissolved in 160 ml of 90% AcOH under heating. 29.41 g of t-BuOCl was added dropwise to the solution while it was kept at 35° to 40° C. The solution was stirred at room temperature for 3 hours and then 200 ml of ether was added thereto. The mixture was left to stand overnight and crystals thus formed were separated by filtration and washed with ether. 42.0 g of the crude crystals were recrystallized from acetonitrile to obtain 35 g of 2-chloro-3-hydroxy-4-methoxybenzaldehyde (69%).