Vanillin → 2-hydroxy-N-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-(4-methoxyphenyl)acetamide
Reaction equation
O=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[OH:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[C:14]([NH:16][NH2:17])=[O:15]>C(O)C>[OH:9][C:8]1[CH:10]=[CH:11][C:3](/[CH:2]=[N:17]/[NH:16][C:14](=[O:15])[CH:13]([OH:12])[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:4][C:5]=1[O:6][CH3:7]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Vanillin (23 g, 0.15 mol) is added to a solution of hydroxy-(4-methoxy-phenyl)-acetic acid hydrazide (30 g, 0.15 mol) in 300 ml of ethanol at room temperature. After heating this mixture to reflux for 4 hours, the reaction is poured on water and extracted with ethyl acetate. The combined organic layer is washed with brine, dried over magnesium sulfate and evaporated. The residue, which is hydroxy-(4-methoxy-phenyl)-acetic acid [1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide, is sufficiently pure to be directly used in the next step.