2-Indanone → 2-Indanone

Participants

Reaction Steps

A suspension of anhydrous cerium chloride (40.60 g, 164.7 mmol) in THF(250 mL) was stirred at room temperature for 2 hours under nitrogen. o-Tolylmagnesium bromide (70.0 mL of 2.0M solution in diethyl ether, 140.0 mmol) was added at 0° C. and stirred for 3.5 h. A solution of 2-indanone (14.21 g, 107.7 mmol) in THF (20 mL) was added at the same temperature. After stirring at 0° C. for 3 h, the mixture was allowed to warm to room temperature and kept at ambient temperature overnight (12 h). It was then treated with 5% aqueous hydrochloric solution. The solution was extracted with diethyl ether (4*200 mL). All etheral layers were combined, washed with water (100 mL), dried over anhydrous magnesium sulphate and concentrated to give the crude product. Kugelrohr distillation (120° C./0.3 mm Hg) yielded 4.0 g of 2-indanone and 10.38 g of 2-(o-tolyl)-2-indanol in solid form. 1 H-N.M.R. (CDCl3) d 2.13 (br s, 1H), d 2.52(s, 3H), d 3.36 (d, J=16.2 Hz, 2H), d 3.63 (d, J=16.2 Hz, 2H), d 7.15-7.62 (m, 8H)

Provenance & Evidence