Toluene → 1-(3,3-Dimethylcyclohexyl)ethanone

Participants

Reaction Steps

A slurry of 1-acetyl-3,3-dimethylcyclohexane (624 grams, 4 moles), granular sodium hydroxide (240 grams, 6 moles), Aliqu t® 336 (tricaprylmethylammonium chloride [35 grams]), methallyl chloride (432 grams, 4.8 moles), and 400 ml of toluene is heated at reflux for 4 1/4 hours. At the end of this time, one liter of water is added to the cooled reaction mass. The aqueous layer is discarded, and the organic layer is distilled rapidly through a short column to afford 203 grams of recovered 1-acetyl-3,3-dimethylcyclohexane, 500 grams of 1-acetyl-3,3-dimethyl-1-methallylcyclohexane, and 73 grams of 3,3-dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl)cyclohexane) (1°-4°, 3.0 mm Hg) containing 5% of 3,3-dimethyl-1-(4-methyl-4-pentenoyl). A portion of the latter compound is isolated by GLC chromatography (1 foot × 1/4 inch 80% SE-30 packed column; 200° C isothermal) and exhibits the following odor and flavor properties:

Provenance & Evidence