3-Chloro-2,2-dimethylpropanoyl chloride → 3-chloro-N-hydroxy-2,2-dimethylpropanamide

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Reaction Steps

To a solution of hydroxylamine hydrochloride (50.0 g, 0.7195 mol) in 150 mL of water, 50% aqueous sodium hydroxide solution is added dropwise until a pH of 7.0-7.2 is obtained. The solution is cooled to 20°-25° C. and 3-chloropivaloyl chloride (100.0 g, 0.6426 mol) is added dropwise maintaining a pH of 7.0-7.2 with 50% aqueous sodium hydroxide solution and a reaction pot temperature <30° C. The total addition time is 1 hour. This yellow slurry is stirred at room temperature overnight then diluted with water (200 mL). The hydroxamic acid is extracted with ethyl acetate (2×200 mL) and washed with water (200 mL). The organic layer is dried over magnesium sulfate and concentrated to 46.3 g of the title compound as a yellow solid and used without further purification.

Provenance & Evidence