Sodium Chloride → (5-Methylpyridin-2-yl)methanol

HRID 1413111Notes

Reaction equation

HRID 1413111 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1)(=O)C.[OH-].[Na+].[Cl-].[Na+]>O>[OH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 123253842-Pyridinemethanol, 5-methyl-, 2-acetate

Product 1

HCID 12325387(5-Methylpyridin-2-yl)methanolYield 83.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

14.0 g of 2-acetoxymethyl-5-methylpyridine were heated under reflux for 90 minutes in a solution of 4.5 g of sodium hydroxide in 150 ml of water. The cooled solution was saturated with sodium chloride and extracted with a total amount of 100 ml of chloroform. The organic phases were washed with saturated sodium chloride solution, dried over magnesium sulphate, and concentrated by evaporation at 40°/16 mm Hg. The oil obtained distilled at 12°/8 mm Hg. 8.7 g of 2-hydroxymethyl-5-methylpyridine were obtained.

Workup

  1. extractionextracted with a total amount of 100 ml of chloroform
  2. washThe organic phases were washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated by evaporation at 40°/16 mm Hg
  5. customThe oil obtained
  6. distillationdistilled at 12°/8 mm Hg

Sources & evidence

ORD record
ord-f66572b26c954003ade6765168c13688
Source dataset
uspto-grants-1981_02
Patent number
US04248880

Reaction notes

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