Pale yellow to brown low melting solid
o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII).
o-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII). It is also used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.
A positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin.
ChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.
ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD50 of 1330 mg/kg in mice.
o-Vanillin induces DNA damage as detected by comet assay.
GENERAL METHOD: A mixed solution of 3-methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (53 μL, 0.20 mmol) with N-formylpiperidine (2.0 mmol) in acetonitrile (1.4 mL) was added to tetrabutylammonium fluoride (TBAF, 1.0 M acetonitrile solution, 0.60 mL, 0.60 mmol) under argon protection at room temperature. After the reaction mixture was stirred at the same temperature for 3 h, water (0.1 mL) was added. Subsequently, the reaction mixture was concentrated under reduced pressure. The residue was purified by fast silica gel column chromatography with the eluent ethyl acetate/hexane (1/20 to 1/8 containing 2% dichloromethane) to afford the target products 1-(3-methoxyphenyl)piperidine and o-vanillin.
[1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189
