Sodium Hydroxide → (4-Methoxy-5-methylpyridin-2-yl)methanol

HRID 979868Notes

Reaction equation

HRID 979868 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([CH3:14])=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH3:13][O:12][C:10]1[C:9]([CH3:14])=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22151432(4-Methoxy-5-methyl-2-pyridyl)methyl acetate

Product 1

HCID 15163463(4-Methoxy-5-methylpyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

47.8 g of (4-methoxy-5-methyl-2-pyridyl)methyl acetate were dissolved in 330 ml of ethanol. 165 ml of 3N sodium hydroxide solution were then added dropwise thereto at 0° and the mixture was stirred at room temperature for a further 3 hours. The ethanol was subsequently removed in vacuo, whereupon the residual aqueous solution was extracted three times with 250 ml of methylene chloride. The organic extracts were dried over sodium sulfate and evaporated in vacuo. The residue crystallizes from petroleum ether and there was obtained 4-methoxy-5-methyl-2-pyridylmethanol of melting point 101°-103°.

Workup

  1. customThe ethanol was subsequently removed in vacuo, whereupon the residual aqueous solution
  2. extractionwas extracted three times with 250 ml of methylene chloride
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue crystallizes from petroleum ether

Sources & evidence

ORD record
ord-33a7517123d945b9887ac612b6e7af31
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

Loading…