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

HRID 703178Notes

Reaction equation

HRID 703178 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 hyroxide 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-a3a2589e6e8c4264bd69b0e31d4b5ac7
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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