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

HRID 35471Notes

Reaction equation

HRID 35471 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 are dissolved in 570 ml of ethanol. 285 ml of 3N sodium hydroxide solution are then added dropwise thereto at 0° and the mixture is stirred at room temperature for 3 hours. The ethanol is subsequently removed in vacuo, whereupon the residual aqueous solution is extracted three times with 300 ml of methylene chloride. The organic extracts are dried over sodium sulphate and evaporated in vacuo. The residue is crystallized from petroleum ether and there is obtained 4-methoxy-3,5-dimethyl-2-pyridylmethanol of melting point 49°-51°.

Workup

  1. customThe ethanol is subsequently removed in vacuo, whereupon the residual aqueous solution
  2. extractionis extracted three times with 300 ml of methylene chloride
  3. dry with materialThe organic extracts are dried over sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-a95135df88a74dd8b718c179bb37ce5a
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

Loading…