2-Cyclohexen-1-one, 4,4-dimethyl- → Cyclohexanone, 4,4-dimethyl-

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Reaction Steps

This compound was prepared according to the method described by H-J Liu, et al., (Can. J. Chem. (1988), 66, 2345) with modification. To a three-neck round-bottomed flask was added palladium on carbon (Degussa Type, 10% wt. (dry basis)) (0.167 g). The flask was evacuated and then filled with nitrogen and the evacuation/fill cycle was repeated twice more. To the flask was added a solution of 4,4-dimethyl-2-cyclohexene-1-one (2.1 mL, 2.0 g, 16 mmol) in EtOAc (100 mL). The flask was evacuated and then filled with nitrogen and the evacuation/fill cycle was repeated once more. The flask was evacuated and then filled with hydrogen using a balloon. The reaction mixture was stirred under a hydrogen atmosphere at room temperature overnight. The flask was evacuated and filled with nitrogen. The reaction mixture was filtered through a pad of Celite and the pad was washed with EtOAc. The filtrate was concentrated to give 1.63 g (82%) of compound 20 as a colorless liquid that solidified to a white solid. 1H NMR is consistent with that reported in the cited reference. 1H NMR (400 MHz, CDCl3): δ 1.08 (s, 6H), 1.65 (t, J=6.9 Hz, 4H), 2.33 (t, J=6.9 Hz, 4H).

Provenance & Evidence