Hydrochloric Acid → 1-(1-(4-(Trifluoromethyl)phenyl)cyclobutyl)ethanone

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Reaction Conditions

Reaction Steps

The starting nitrile, 1-(4-Trifluoromethyl-phenyl)-cyclobutanecarbonitrile, has been described (Parke Davis & Co., U.S. Pat. No. 3,536,656; 1970 and Chemical Abstracts 1970, 73, 109539). To the carbonitrile (2 g) in 5 mL of toluene in a pressure tube was added 10 mL of 3M MeMgBr ether solution (3 equiv.). The tube was sealed and the reaction mixture was heated at 95° C. for 24 hr, cooled to room temperature, poured into 50 mL of water, acidified with 25 mL of 5 M HCl, and this solution was heated at 70° C. for 2 h, cooled, and extracted with ether. The extracts were dried, filtered, concentrated, and purified on silica gel to give pure 1-[1-(4-trifluoromethyl-phenyl)-cyclobutyl]-ethanone (1.9 g, 88%). Data for this ketone: MS 242 (M); 1H NMR (300 MHz, CDCl3) δ 7.6 (d, 8.0 Hz, 2H), 7.4 (d, 8.0 Hz, 2H), 2.75–2.85 (m, 2H), 2.35–2.5 (m, 2H), 1.8–2.0 (3H s and 2H m overlapping); 13C NMR (75 MHz, CDCl3): δ 207.7, 147.5, 129.5, 126.9, 126.1, 125.9 (CF3), 59.5, 30.9, 24.6, 16.1.

Provenance & Evidence