Water → 1-Hydroxy-3-(4-methoxyphenyl)propan-2-one

Participants

Reaction Steps

4-Allylanisole (98%; 3.0 g; 19.86 mmol) was dissolved in glacial acetic acid (180 ml), water (180 ml) and acetone (180 ml). KMnO4 (4.7 g; 29.79 mmol) was added over the course of 1 h. The mixture was then stirred at (RT) for 1 h. It was then decolorized with saturated NaHCO3 solution. The reaction volume was reduced in a rotary evaporator. This was followed by extraction with CH2Cl2, washing of the organic phase with water and drying over Na2SO4. The solvent was then removed in a rotary evaporator. The oily residue was purified by column chromatography (SiO2; EtOAc/n-heptane 1:2). 1-Hydroxy-3-(4-methoxyphenyl)propan-2-one was obtained as a white crystalline powder. MS: 81.20 (M+H); Rt: 0.83 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

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