Hydrogen Peroxide → 4-(2-Hydroxyethoxy)-2-methoxyphenol

Beteiligte Stoffe

Reaktionsschritte

A solution of 4-(2-hydroxyethoxy)-2-methoxybenzaldehyde (465.6 mg, 2.373 mmol) and 30 wt % hydrogen peroxide (0.313 mL, 3.04 mmol) in conc. H2SO4 (0.0475 mL) and MeOH (4.75 mL) was stirred overnight at 25° C. under N2. After this time the mixture was diluted with water (20 mL) and extracted with CH2Cl2 (3×30 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 25M, Si, ˜20 mL/min, 100% hexanes for 144 mL, gradient to 55% EtOAc in hexanes over 2394 mL, gradient to 100% EtOAc over 999 mL) to afford 4-(2-hydroxyethoxy)-2-methoxyphenol, as a colorless oil. Rf=0.30 (50% EtOAc/hexanes). LCMS calc.=207.1; found=206.9 (M+Na)+. 1H NMR (500 MHz, CHCl3): δ 6.77 (d, J=8.6 Hz, 1 H); 6.47 (d, J=2.8 Hz, 1 H); 6.34 (dd, J=8.7, 2.8 Hz, 1 H); 5.82 (s, 1 H); 3.98 (t, J=4.6 Hz, 2 H); 3.90 (t, J=4.5 Hz, 2 H); 3.76 (s, 3 H); 2.96 (s, 1 H).

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