反应详情

MnO2 (3.40 g, 39.2 mmol) was added to a stirring solution of (3-chloro-2-propoxyphenyl)methanol (1.12 g, 5.60 mmol) in benzene (54 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth, the pad rinsed with CH2Cl2 (100 mL), and the solution concentrated to a clear oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 98:2) gave the title compound (0.42 g, 38%) as a clear oil: 1H NMR (300 MHz, DMSO-d6) δ 10.27 (s, 1H), 7.85 (d, J=1.6 Hz, 1H), 7.73 (d, J=1.6 Hz, 1H), 7.32 (t, J=7.8 Hz, 1H), 4.04 (t, J=6.4 Hz, 2H), 1.85-1.78 (m, 2H), 1.03 (t, J=7.3 Hz, 3H).

1. filtrationthe solution was filtered over diatomaceous earth
2. washthe pad rinsed with CH2Cl2 (100 mL)
3. concentrationthe solution concentrated to a clear oil
4. customPurification by column chromatography (silica gel, hexanes/EtOAc, 98:2)