Sodium Hydroxide → 4-Ethoxy-5-methyl-2-pyridylmethanol

HRID 979873Notes

Reaction equation

HRID 979873 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]([CH3:15])=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH2:13]([O:12][C:10]1[C:9]([CH3:15])=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[CH:11]=1)[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22151443(4-Ethoxy-5-methyl-2-pyridyl)methyl acetate

Product 1

HCID 221514614-Ethoxy-5-methyl-2-pyridylmethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.4 g of (4-ethoxy-5-methyl-2-pyridyl)methyl acetate were dissolved in 46 ml of ethanol. 23 ml of 3N sodium hydroxide solution were then added dropwise thereto 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 100 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-ethoxy-5-methyl-2-pyridylmethanol of melting point 99°-101°.

Workup

  1. customThe ethanol was subsequently removed in vacuo, whereupon the residual aqueous solution
  2. extractionwas extracted three times with 100 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-03d91ae3e0694e4fa802ef5f2b96e009
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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