Hydrochloric Acid → 3-Tert-butyl-6-phenyl-1,6-dimethyl-fulvene

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Reaction Steps

To a 100-ml three-neck flask, 1.50 g of potassium hydroxide pulverized in mortar, 0.91 g of 18-crown-6 and 45 ml of THF were charged under nitrogen atmosphere. 2.70 g of t-butyl-methylcyclopentadiene was added dropwise thereto over 10 minutes in a water bath, and the mixture was stirred for 3 hours. The solution was added with 11.33 g of acetophenone dropwise over 10 minutes, and the mixture was stirred for 22 hours. The reaction solution was poured into 100 ml of 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted with 200 ml of hexane. The separated organic layers were combined, and washed with a saturated aqueous solution of sodium hydrogen carbonate, water, and a saturated aqueous solution of sodium chloride. After the solution was dried over magnesium sulfate, the solvent was distilled off, and the obtained product was purified by column chromatography. The yield was 1.98 g. Identification was performed by 1H-NMR spectrum. The measurement result is shown as follows. The result of the 1H-NMR spectrum proved that the obtained compounds are a mixture of the isomers.

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