反应详情

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.)

1. customThe reaction volume was reduced in a rotary evaporator
2. extractionThis was followed by extraction with CH2Cl2
3. washwashing of the organic phase with water
4. dry with materialdrying over Na2SO4
5. customThe solvent was then removed in a rotary evaporator
6. customThe oily residue was purified by column chromatography (SiO2; EtOAc/n-heptane 1:2)