Isopropanol → 2-(2-Methoxyphenyl)cyclopentan-1-one

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[OH:14].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][C:10]1=[O:14]

Participants

Procedure

To a solution of 2-(2-methoxyphenyl)cyclopentanol (9.11 g, 47.4 mmol) in Acetone (Volume: 474 ml) was added Jones reagent (6.52 ml, 52.1 mmol) (8.0 M). After the addition was complete (the conversion of red reagent to green solid, and the supernatant solution took on the color of unreacted reagent), isopropanol was added to quench the excess reagent. The green solid was filtered off through ceilite and rinsed with acetone. The filtrate was concentrated and purified by flash chromatography to get 2-(2-methoxyphenyl)cyclopentanone (6.64 g, 34.9 mmol, 73.6% yield). LC-MS (M+H)+=191.0. 1H NMR (500 MHz, CD3OD) δ 7.24 (td, J=7.8, 1.8 Hz, 1H), 7.09 (dd, J=7.5, 1.7 Hz, 1H), 6.95 (d, J=8.2 Hz, 1H), 6.90 (td, J=7.4, 1.1 Hz, 1H), 3.77 (s, 3H), 3.43-3.37 (m, 1H), 2.48-2.30 (m, 3H), 2.23-2.11 (m, 2H), 2.00-1.88 (m, 1H).