Isopropanol → HCID 825700, compound

Participants

Reaction Steps

6-chloro-1,1-dimethylindane (2.19 g, 0.0121 mol) was dissolved in acetone (50 mL), and 1.41 M solution of magnesium sulfate in water (9.02 mL) was added, followed by potassium permanganate (3.83 g, 0.0242 mol). The mixture was stirred at room temperature overnight. 1:1 water:isopropanol was then added to the mixture and this was stirred for 1 hour. The mixture was then evaporated to an aqueous residue and ethyl acetate was added. The mixture was filtered, washing the collected solids with EtOAc, and the filtrates were separated. The organic phase was concentrated, and the residue was purified by silica gel chromatography, eluting with 20 to 100% dichloromethane in hexanes to yield the product, 1.25 g (46%). 1H-NMR (400 MHz, CDCl, δ) 7.62 (d, J=8.3 Hz, 1H), 7.47 (d, J=1.6 Hz, 1H), 7.34 (dd, J=1.8 Hz, 8.1 Hz, 1H), 2.60 (s, 2H), 1.42 (s, 6H).

Provenance & Evidence