Thionyl Chloride → 3-(Chloromethyl)-2,4-dimethylpyridine

HRID 1692Notes

Reaction equation

HRID 1692 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8]O)=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.S(Cl)([Cl:13])=O>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][Cl:13])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 103293512,4-Dimethyl-3-pyridinemethanol

Product 1

HCID 196909773-(Chloromethyl)-2,4-dimethylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bfc9e545236f4da9864ea3f99c2d6fe8
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Reaction notes

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