Thionyl Chloride → 2-Methyl-3-hydroxy-4-chloromethyl-5-vinylpyridine hydrochloride

HRID 223530Notes

Reaction equation

HRID 223530 reaction equation
[ClH:1].[CH3:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:10]O)[C:6]([CH:12]=[CH2:13])=[CH:5][N:4]=1.S(Cl)([Cl:16])=O>O1CCCC1>[ClH:16].[CH3:2][C:3]1[C:8]([OH:9])=[C:7]([CH2:10][Cl:1])[C:6]([CH:12]=[CH2:13])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202639332-Methyl-3-hydroxy-4-hydroxymethyl-5-vinylpyridine hydrochloride

Product 1

HCID 202639722-Methyl-3-hydroxy-4-chloromethyl-5-vinylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.65 g. of 2-methyl-3-hydroxy-4-hydroxymethyl-5-vinylpyridine hydrochloride, 1 ml. of thionyl chloride and 20 ml. of tetrahydrofuran is refluxed 6 hours. After cooling, the precipitate is collected on a filter, washed with ether and dried to give 2-methyl-3-hydroxy-4-chloromethyl-5-vinyl pyridine hydrochloride.

Workup

  1. additionA mixture of 1.65 g
  2. temperatureAfter cooling
  3. customthe precipitate is collected on a filter
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-893f1d7b62bc40ad9de8b959cd002aad
Source dataset
uspto-grants-1982_10
Patent number
US04355034

Reaction notes

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