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

HRID 703172Notes

Reaction equation

HRID 703172 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-ef6d1dc9131f4033be5a48cc3ab03cb3
Source dataset
uspto-grants-1991_01
Patent number
US04981861

Reaction notes

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