4-Hydroxybenzaldehyde → 4-(Phenethylaminomethyl)phenol

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Reaction Steps

Dissolve 4-hydroxybenzaldehyde (1.00 g, 8.12 mmol) in methanol (40.6 mL). Add 3 Å molecular sieves and phenethylamine (1.02 mL, 8.12 mmol). Stir at room temperature for 17 hours. Add NaBH4 (0.341 g, 9.01 mmol). After five hours, filter and concentrate. Purify by 10 g SCX column washing with methanol and eluting with 2.0 M NH3 in methanol to give the title compound as an off white solid: HRMS calcd for C15H18NO 228.1388 (M+H)+, found 228.1387, time 0.74 min, MS TOF ES+ 228.1 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=1.4 min, 100% purity.

Provenance & Evidence