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

HRID 1975469Notes

Reaction equation

HRID 1975469 reaction equation
O[CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.S(Cl)([Cl:12])=O>C1(C)C=CC=CC=1.[OH-].[Na+]>[Cl:12][CH2:2][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 302564(2-Methylpyridin-3-yl)methanol

Product 1

HCID 122437113-(Chloromethyl)-2-methylpyridine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-hydroxymethyl-2-methylpyridine (10.42 g) in toluene (100 ml) was added dropwise thionyl chloride (9.87 ml) at 25° C. After 2.5 hours, the solvent was removed in vacuo to give a residual solid. The solid was dissolved in 4N-aqueous sodium hydroxide (100 ml) and extracted with ethyl acetate. The organic layer was separated, washed with brine and dried over magnesium sulfate. Concentration of the solution gave 3-chloromethyl-2-methylpyridine (9.22 g).

Workup

  1. customthe solvent was removed in vacuo
  2. customto give a residual solid
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-30c44a74223d4702b9f7c475228d187a
Source dataset
uspto-grants-1994_02
Patent number
US05286721

Reaction notes

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