2-Chloro-4-methylpyridine → 2-Methoxy-4-methylpyridine

Commercially available 2-chloro-4-methylpyridine (25.5 g, 200 mmol) and a sodium methoxide-methanol solution (28.0%, 77.0 g, 399 mmol) were mixed, and the mixture was heated under reflux for 15 hours. After completion of the reaction was confirmed by thin-layer chromatography, the resulting precipitate was filtered out, and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the resulting mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was, evaporated under reduced pressure to give 2-methoxy-4-methylpyridine (18.4 g, yield 75%).

1. temperaturethe mixture was heated
2. temperatureunder reflux for 15 hours
3. filtrationthe resulting precipitate was filtered out
4. concentrationthe filtrate was concentrated under reduced pressure
5. additionWater was added to the residue
6. extractionthe resulting mixture was extracted with dichloromethane
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. customevaporated under reduced pressure

ORD record

ord-c1bc6646e20b4b2a8d7b722504a7578d

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956060B2