Sodium Hydroxide → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

HRID 979855Notes

Reaction equation

HRID 979855 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH3:14])[C:9]([CH3:15])=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH3:14][O:13][C:10]1[C:9]([CH3:15])=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50672892-(Acetoxymethyl)-4-methoxy-3,5-dimethylpyridine

Product 1

HCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

94.9 g of (4-methoxy-3,5-dimethyl-2-pyridyl)methyl acetate were dissolved in 570 ml of ethanol. 285 ml of 3N sodium hydroxide solution were then added dropwise thereto at 0° and the mixture was stirred at room temperature for 3 hours. The ethanol was subsequently removed in vacuo, whereupon the residual aqueous solution was extracted three times with 300 ml of methylene chloride. The organic extracts were dried over sodium sulfate and evaporated in vacuo. The residue was crystallized from petroleum ether and there was obtained 4-methoxy-3,5-dimethyl-2-pyridylmethanol of melting point 49°-51°.

Workup

  1. customThe ethanol was subsequently removed in vacuo, whereupon the residual aqueous solution
  2. extractionwas extracted three times with 300 ml of methylene chloride
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was crystallized from petroleum ether

Sources & evidence

ORD record
ord-68903e33bba741efa5fbeadff17bcbf8
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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