Hydrochloric Acid → 4-Dimethylamino-4-(3-fluorophenyl)cyclohexanecarbaldehyde

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Reaction Steps

A 60% dispersion of sodium hydride in mineral oil (254 mg, 6.36 mmol) was added to a suspension of methoxymethyltriphenylphosphonium chloride (2.18 g, 6.36 mmol) in anhydrous tetrahydrofuran (5 ml) and anhydrous N,N-dimethylformamide (5 ml) under argon. The mixture was stirred at room temperature for 2 h. A solution of 4-dimethylamino-4-(3-fluorophenyl)cyclohexanone (1.0 g, 4.24 mmol) in anhydrous tetrahydrofuran (5 ml) and anhydrous N,N-dimethylformamide (5 ml) was then added dropwise in the course of 30 min and the mixture was stirred at room temperature overnight. 2 M hydrochloric acid (25 ml) was then added dropwise, while cooling with ice, and the mixture was stirred at room temperature for 5 h. Thereafter, the mixture was extracted with ethyl acetate (5×20 ml) and diethyl ether (3×20 ml). The aqueous phase was adjusted to pH 11 with 4 M sodium hydroxide solution and extracted with ethyl acetate (4×20 ml). The combined organic extracts from the alkaline solution were dried with sodium sulfate and concentrated i. vac.

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