(3-Isopropyl-2-propoxyphenyl)methanol → 3-Isopropyl-2-propoxybenzaldehyde
Reaction equation
[CH:1]([C:4]1[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[C:6]([CH2:10][OH:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]>C1C=CC=CC=1.O=[Mn]=O>[CH:1]([C:4]1[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]=[O:11])([CH3:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
MnO2 (6.88 g, 79.2 mmol) was added to a stirring solution of (3-isopropyl-2-propoxyphenyl)methanol (2.75 g, 13.2 mmol) in benzene (130 mL) under N2. After stirring for 48 h, the solution was filtered over diatomaceous earth, the pad rinsed with CH2Cl2 (200 mL) and the solution concentrated to a yellow oil. Purification by column chromatography (silica gel, hexanes/EtOAc, 100 to 98:2) gave the title compound (1.49 g, 54%) as a light yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.67 (dd, J=7.6, 1.7 Hz, 1H), 7.59 (dd, J=7.6, 1.7 Hz, 1H), 7.28 (t, J=7.6 Hz, 1H), 3.87 (t, J=6.4 Hz, 2H), 3.35-3.30 (m, 2H), 1.85-1.78 (m, 2H), 1.21 (t, J=6.9 Hz, 7H), 1.03 (t, J=7.3 Hz, 3H).