Sodium Hydroxide → 4-Ethoxy-3,5-dimethyl-2-pyridylmethanol

HRID 979862Notes

Reaction equation

HRID 979862 reaction equation
C([O:4][CH2:5][C:6]1[C:11]([CH3:12])=[C:10]([O:13][CH2:14][CH3:15])[C:9]([CH3:16])=[CH:8][N:7]=1)(=O)C.[OH-].[Na+]>C(O)C>[CH2:14]([O:13][C:10]1[C:9]([CH3:16])=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[C:11]=1[CH3:12])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22151469(4-Ethoxy-3,5-dimethyl-2-pyridyl)methyl acetate

Product 1

HCID 199637424-Ethoxy-3,5-dimethyl-2-pyridylmethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

32.9 g of (4-ethoxy-3,5-dimethyl-2-pyridyl)methyl acetate were dissolved in 190 ml of ethanol. 95 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 and the residual aqueous solution was extracted three times with 200 ml of methylene chloride. The organic extracts were dried over sodium sulfate and evaporated in vacuo. The residue crystallized from petroleum ether and there was obtained 4-ethoxy-3,5-dimethyl-2-pyridylmethanol of melting point 58°-59°.

Workup

  1. customThe ethanol was subsequently removed in vacuo
  2. extractionthe residual aqueous solution was extracted three times with 200 ml of methylene chloride
  3. dry with materialThe organic extracts were dried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue crystallized from petroleum ether

Sources & evidence

ORD record
ord-56996fc754c547429746aec39ca9f110
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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