Reaction #487538

Reaction equation

water

N,O-dimethylhydroxyamine hydrochloride

Decanoic acid

→

N-methoxy-N-methyldecanamide

Yield 97.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas then added to the solution
2. 2
   workup.STIRRINGthe obtained mixture was further stirred for 3 hours
3. 3
   Extractionthe reaction solution was extracted with dichloromethane two times
4. 4
   workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
5. 5
   Otherto dry it
6. 6
   Filtrationthe resultant was filtrated
7. 7
   Concentrationwas then concentrated
8. 8
   OtherThe obtained residue was purified

Procedure

Decanoic acid (4 g, 23.2 mmol) was dissolved in an anhydrous dichloromethane solution (80 mL), and 1,1-carbonyldiimidazole (4.5 g, 27.9 mmol) was then added to the solution, followed by stirring for 1.5 hours. Subsequently, N,O-dimethylhydroxyamine hydrochloride (2.7 g, 27.9 mmol) was added to the reaction solution, and the obtained mixture was further stirred for 3 hours. After addition of distilled water, the reaction solution was extracted with dichloromethane two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane:ethyl acetate=8:1), so as to obtain N-methoxy-N-methyldecanamide (4.8 g, 97%) as an amide body in the form of a colorless transparent liquid.

Source