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. p-Tolylmagnesium bromide (100.0 mL of 1.0M solution in diethyl ether, 100.0 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 yielded 2.94 g of 2-indanone (110° C./0.3 mm Hg) and 17.27 g of 2-(p-tolyl)-2-indanol (160° C./0.3 mm Hg) in solid form. 1H-N.M.R. (CDCl3) d 2.17 (br s, 1H), d 2.35 (s, 3H), d 3.22 (d, J=16.2 Hz, 2H), d 3.50 (d, J=16.2 Hz, 2H), d 7.15-7.30 (m, 6H), d 7.45(br d, J=7.1 Hz, 2H).

Provenance & Evidence