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

Beteiligte Stoffe

Reaktionsschritte

To a 100 ml three-neck flask equipped with a magnetic stirrer chip and a three-way cock, 1.50 g (25.8 mmol) of potassium hydroxide pulverized in mortar, 0.91 g (3.44 mmol) of 18-crown-6 and 45 ml of THF were charged under a nitrogen atmosphere. Thereto in a water bath, 2.70 g (16.0 mmol) of 1-tert-butyl-3-methylcyclopentadiene was added dropwise over 10 minutes and stirred for 3 hours. The solution was added with 11.33 g (94.3 mmol) of acetophenone dropwise over 10 minutes, and 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 twice with 200 ml of hexane. The separated organic layers were combined, washed with a saturated aqueous solution of sodium hydrogencarbonate, water, and saturated aqueous solution of sodium chloride. After the solution was dried over magnesium sulfate, the obtained product was purified by column chromatography to obtain 1.98 g of a red orange liquid. The yield was 52%. Identification was done by 1H-NMR spectrum and FD-mass analysis spectrum. The result of the 1H-NMR spectrum proved that the obtained compounds are mixture of isomers. The measurement results are shown as follows.

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