Thionyl Chloride → 2-Chloromethyl-4-(2-hydroxyethoxy)-3-methylpyridine

11.9 g of the 4-(2-hydroxyethoxy)-2-hydroxymethyl-3-methylpyridine prepared above was dissolved in 200 ml of dichloromethane to obtain a solution. 24 ml of thionyl chloride was dropwise added to this solution at 0° C. The obtained mixture was stirred at a room temperature for 2 hours and distilled under a reduced pressure to remove the dichloromethane and excess thionyl chloride. A saturated aqueous solution of sodium hydrogencarbonate was added to the residue to obtain a mixture. This mixture was extracted with chloroform. The extract was dried over magnesium sulfate and filtered. The filtrate was concentrated to obtain 10.9 g of 2-chloromethyl-4-(2-hydroxyethoxy)-3-methylpyridine.

1. customto obtain a solution
2. distillationdistilled under a reduced pressure
3. customto remove the dichloromethane and excess thionyl chloride
4. additionA saturated aqueous solution of sodium hydrogencarbonate was added to the residue
5. customto obtain a mixture
6. extractionThis mixture was extracted with chloroform
7. dry with materialThe extract was dried over magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated

ORD record

ord-1ea98021457f46cc961b024e03050901

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05998445