p-METHYLACETOPHENONE → 6-Methyl-6-(p-tolyl)fulvene

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Reaction Steps

Under a nitrogen atmosphere, a solution of a cyclopentadienyllithium salt (5.9 g, 81.9 mmol) in dry diethyl ether (100 mL) was cooled in an ice bath, and 4′-methylacetophenone (10.0 g, 74.5 mmol) was dropped thereinto. Then, the product was stirred at room temperature for 20 hours to induce a reaction. After the reaction was terminated, dilute aqueous hydrochloric acid was added thereto, the product was subjected to extraction with hexane, the organic layer was subsequently washed with water and then dehydrated with anhydrous magnesium sulfate, and then the solvent was distilled off to produce a red liquid. The red liquid was purified by column chromatography (silica gel, solvent: hexane) to produce 9.8 g of 6-methyl-6-(p-tolyl)fulvene. The analytical values were as follows.

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