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

HRID 2051772Notes

Reaction equation

HRID 2051772 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-6967bcf225d54437807472e7e211d85a
Source dataset
uspto-grants-1980_01
Patent number
US04182766

Reaction notes

Loading…