Diethyl Ether → 2-Chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochloride

HRID 979863Notes

Reaction equation

HRID 979863 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([CH3:10])=[CH:8][N:7]=[C:6]([CH2:11]O)[C:5]=1[CH3:13])[CH3:2].S(Cl)([Cl:16])=O.CCOCC>C(Cl)Cl>[ClH:16].[Cl:16][CH2:11][C:6]1[C:5]([CH3:13])=[C:4]([O:3][CH2:1][CH3:2])[C:9]([CH3:10])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 199637424-Ethoxy-3,5-dimethyl-2-pyridylmethanol

Product 1

HCID 221514582-Chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21.0 g of 4-ethoxy-3,5-dimethyl-2-pyridylmethanol, dissolved in 110 ml of methylene chloride, were added dropwise at 0° to 10 ml of thionyl chloride in 220 ml of methylene chloride. After stirring at room temperature for 16 hours 890 ml of ether were added dropwise thereto while cooling and the mixture was stirred at room temperature for a further 2 hours. The separated crystals were filtered off under suction and washed with ether. There was obtained 2-chloromethyl-4-ethoxy-3,5-dimethylpyridine hydrochloride of melting point 156°-158°.

Workup

  1. additionwere added dropwise
  2. temperaturewhile cooling
  3. filtrationThe separated crystals were filtered off under suction
  4. washwashed with ether

Sources & evidence

ORD record
ord-484d99e0257c43e6aab5de40fc10ab58
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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