Hydrochloric Acid → 2-(2,4-Dichlorophenyl)hexyl amine

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Reaction Steps

To a suspension of 9.0 g (0.24 mole) of lithium aluminum hydride in 200 ml of anhydrous ether is added 57 g (0.24 m) of α-n-butyl-2,4-dichlorobenzyl cyanide dropwise at 10°. The reaction mixture is stirred at room temperature for 30 minutes and at 35° overnight. Excess lithium aluminum hydride is then decomposed by addition of saturated ammonium chloride solution (50 ml), followed by 20% hydrochloric acid (300 ml) at 0°. The acidic aqueous layer is separated and extracted with ether. The combined ether portions are washed with water and dried over MgSO4. When ether is evaporated under vacuo, there is obtained 63 g of a yellow solid. The solid is then dissolved in 20% sodium hydroxide solution and extracted with ether. The combined ether extracts are dried over MgSO4. Solvent is evaporated to give 48 g of an oil. Vacuum distillation (101°-104°/0.1 mm) gives 38.3 g of pure product.

Provenance & Evidence