Toluene → 1-Acetyl-3,3-dimethyl-1-(2-methyl-2-propenyl)cyclohexane

Participants

Reaction Steps

A slurry of 1-acetyl-3,3-dimethylcyclohexane (624 grams, 4 moles), granular sodium hydroxide (240 grams, 6 moles), Aliquot® 336 (tricaprylmethylammonium chloride [35 grams]), methallyl chloride (432 grams, 4.8 moles), and 400 ml of toluene is heated at reflux for 41/4 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 (104°, 3.0 mm Hg, containing 5% 3,3-dimethyl-(4-methyl-4-pentenoyl)cyclohexane) and 73 grams of 3,3-dimethyl-1-(2-methallyl-5-methyl-4-pentenoyl) cyclohexane. A portion of the latter compound is isolated by GLC chromatography (1' × 1/4 inch 80% SE-30 packed column; 200° C. isothermal) and exhibits the following odor and flavor properties.

Provenance & Evidence