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

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.

1. customis obtained
2. temperatureThe solution is cooled to 20°-25° C.
3. customa reaction pot temperature <30° C
4. additionThe total addition time
5. extractionThe hydroxamic acid is extracted with ethyl acetate (2×200 mL)
6. washwashed with water (200 mL)
7. dry with materialThe organic layer is dried over magnesium sulfate
8. concentrationconcentrated to 46.3 g of the title compound as a yellow solid
9. customused without further purification

ORD record

ord-73091171216448c8afa066dae38b8de1

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05066665