3-Hydroxybenzaldehyde → 3-[[[3-(4-Methoxyphenoxy)propyl]amino]methyl]phenol

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Reaction Steps

3-(4-Methoxyphenoxy)propylamine (10.0 g) was dissolved in methanol (50 mL) at room temperature, a solution of 3-hydroxybenzaldehyde (6.7 g) in methanol (50 mL) was added dropwise within 5 minutes at water temperature (about 20° C.), and then the resulting mixture was stirred at room temperature for 20 hours. Then, sodium borohydride (2.1 g)/water (100 mL) was added dropwise at water temperature (about 20° C.) for 5 minutes, and the mixture was stirred at room temperature for 12 hours. Precipitates were removed, washed with water and then dried under reduced pressure at 80° C. for 5 hours. Pale yellow crystals were obtained (13.9 g, 87.4%).

Provenance & Evidence