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

HRID 443279Notes

Reaction equation

HRID 443279 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1.S(Cl)([Cl:12])=O>C1C=CC=CC=1>[Cl:12][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12325388(4-Methylpyridin-2-yl)methanol

Product 1

HCID 126752612-(Chloromethyl)-4-methylpyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-hydroxymethyl-4-methylpyridine (5.48 g, 44.5 mmol) and thionyl chloride (60 mL, 822 mmol) in benzene (150 mL) was stirred at room temp. overnight. The product mixture was concentrated under vacuum. The residue was partitioned between dichloromethane and aqueous sodium bicarbonate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under vacuum to provide the title compound as oil. This alkylating reagent was passed through a small plug of activated basic alumina immediately before use.

Workup

  1. concentrationThe product mixture was concentrated under vacuum
  2. customThe residue was partitioned between dichloromethane and aqueous sodium bicarbonate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-000206fc93154c64a5aedfe76e8d6694
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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