Acetone → 4-(3-Oxobutenyl)-benzonitrile

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Water (150 ml) and 10% NaOH aqueous solution (4.5 ml) were added under vigorous stirring to a solution of 4-cyanobenzaldehyde (7.0 g, 80.6 mmol) in acetone (40 ml) and water(25 ml). The reaction mixture was stirred at 14° C. for 8 hr, after the reaction completed, the reaction mixture was neutralized with 6N hydrochloric acid to adjust pH=7-8.The precipitated separated solid was collected by filtration and dried, then recrystallized from anhydrous ethanol to give 4.8 g of crystals in needles, mp: 102-103° C., yield: 49.25%.

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