Hydrochloric Acid → 3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol

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Reaction Steps

Concentrated hydrochloric acid (0.1 mL) was added to 1-(3-methoxymethoxy-phenyl)-2-methylamino-ethanol (300 mg, 1.42 mmol) dissolved in methanol (3 mL). The resulting mixture was heated at reflux for about 30 minutes, and then cooled to ambient temperature. The mixture was concentrated to dryness, and the residue was purified by flash column chromatography on silica gel (1×16 cm, dichloromethane/methanol/ammonium hydroxide=45/8/1 elution) to give the title compound (160 mg, 67%). 1H NMR (300 MHz, CD3OD) δ 7.14 (t, 1H, J=8.1 Hz), 6.81-6.80 (m, 2H), 6.69-6.66 (m, 1H), 4.71-4.67 (m, 1H), 2.78-2.66 (m, 2H), 2.41 (s, 3H); LC-MS: m/z=168 (MH)+; HPLC: 98% (Purity).

Provenance & Evidence