Sodium Hydroxide → (2,6-Dichloropyridin-3-yl)methanol

HRID 1283120Notes

Reaction equation

HRID 1283120 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][O:9]C(=O)C)=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1.[OH-].[Na+]>CO>[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[C:4]([Cl:13])[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12259929HCID 12259929, compound

Product 1

HCID 12259932(2,6-Dichloropyridin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

260 g (1.18 mols) of this 2,6-dichloro-3-acetoxymethylpyridine, 520 ml (2 mols) of aqueous 2N sodium hydroxide solution and 520 ml of methanol are heated under reflux for 2 hours. The methanol is then removed on a rotary evaporator and the residual water phase is extracted by shaking with diethyl ether. After drying the organic phase over magnesium sulphate and concentrating the solution, crude crystalline 2,6-dichloro-3-hydroxymethylpyridine is obtained, which can be purified by recrystallisation from a mixture of cyclohexane/diethyl ether.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe methanol is then removed on a rotary evaporator
  3. extractionthe residual water phase is extracted
  4. dry with materialAfter drying the organic phase over magnesium sulphate
  5. concentrationconcentrating the solution

Sources & evidence

ORD record
ord-ce1a7cd7ee114467987c768c0ed8bb07
Source dataset
uspto-grants-1976_08
Patent number
US03974166

Reaction notes

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