3-Chloro-2-methyl-1-propene → 1-(3,3-Dimethylcyclohexyl)ethanone

Participants

Reaction Conditions

Reaction Steps

A slurry of potassium hydroxide (84 grams, 1.5 moles), 1-acetyl-3,3,-dimethylcyclohexane (156 grams, 1 mole), dibenzo-18-crown-6 (3 grams) having the structure: ##STR19## produced by the Aldrich Chemical Company of Metuchen, New Jersey, and toluene (150 ml) is heated to reflux whereupon the reaction mass thickens. The mass is cooled to 70° C., and methallyl chloride (135 grams, 1.5 moles) is added thereto rendering the reaction mixture more fluid. The reaction mixture is heated at reflux for an additional 9 hours whereupon the mass is cooled, and water is added. The aqueous layer is decanted and the organic layer is distilled to afford 1-acetyl-3,3-dimethylcyclohexane (62 gm) and 1-acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl) cyclohexane (83 gm, NMR spectrum, FIG. 1; IR spectrum, FIG. 2).

Provenance & Evidence