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

HRID 703166Notes

Reaction equation

HRID 703166 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 The residue
  5. customwas crystallized from petroleum ether

Sources & evidence

ORD record
ord-1f1952b0c1cf476b9e6a413c3bc1ce3d
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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