Reaction #1788

Reaction equation

2,4-dimethyl-3-hydroxymethylpyridine

thionyl chloride

→

2,4-dimethyl-3-chloromethylpyridine

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
3. 3
   DryingThe organic layer was dried with MgSO4
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent removed under reduced pressure

Procedure

The 2,4-dimethyl-3-hydroxymethylpyridine (19.2 g, 140 mmol) was dissolved in CH2Cl2 (800 mL) and cooled under nitrogen to 0° C. and thionyl chloride (125 mL) was slowly added and the reaction was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-chloromethylpyridine.

Source