Methanol → 4-[(3,4-Dimethoxyphenylamino)-methyl]-benzoic Acid

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Reaction Steps

To a solution of 3,4-dimethoxy-phenylamine (786 mg; 5.13 mmol) and dibutyltridichloride (219 mg; 0.72 mmol) in ethyleneglycol dimethylether (7 mL), 4-formyl-benzoic acid (748 mg; 4.98 mmol) was added. The suspension was stirred at room temperature for 10 min, treated with phenylsilane (1.0 mL; 7.9 mmol) and the mixture stirred at the same temperature for 12 h. Methanol and a few drops of water were added, stirred for 5 h, concentrated under vacuum, suspended in dichloromethane and stirred for one day at room temperature. After filtration, pure acid 4 (1.13 g; 79% yield) was obtained as a beige solid.

Provenance & Evidence