Synthesis of 2-({[4-(4-{[(E)-1-(2-hydroxy-3-methoxyphenyl) methylidene]amino}phenoxy)phenyl]imino}methyl)- 6 -methoxy phenol

A mixture of 4,4'-diaminodiphenyl ether 1 (1.00 g, 5.00 mmol), o-vanillin 2 (1.52 g, 10.00 mmol) in methanol (40.00 mL) was stirred at room temperature for one hour to give an orange precipitate. Then it was filtered and washed with methanol to give the pure imine 3 (2.27 g, 97.00 %).

m.p. 134-136 °C.

IR (KBr) (cm⁻¹): 1620.4(C=N), 3050-3300 (OH)

¹H-NMR (DMSO) (250 MHz) δ(ppm): 3.87 (6H, s, 2OCH₃), 6.59-7.40 (14H, m, 4Ph), 8.59 (2H, s, N=CH), 13.61 (2H, s, OH)

¹³C-NMR (DMSO) (62.90 MHz) δ(ppm): 56.60 (OCH₃), 115.29-134.1 (aromatic carbons), 161.96 (C=N)

MS (m/z, %): 468(M⁺, 21.5), 406 (HOPh(O)C=NPhOPHN=CPh), 17.5), 242 (CH₃OPhOHC=NPh(O), 6), 150 (CH₃OPhOHC=N, 18.7), 136 (CH₃OPhOHCH, 6.3), 123 (CH₃OPhOH, 10), 119(Ph(O)N=CH, 5.1), 76 (PhH), 43 (C-OCH₃, 100), 41 (C=C-OH, 94).