Methanol → 5-Methoxy-2-methylpyridine

HRID 1789050Notes

Reaction equation

HRID 1789050 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[OH-].[K+].[CH3:11]O>CS(C)=O>[CH3:11][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 142752-Methyl-5-hydroxypyridineHCID 14797Potassium Hydroxide

Product 1

HCID 133587775-Methoxy-2-methylpyridineYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

150 ml of 3-hydroxy-6-methylpyridine are metered into a solution of 84 g of potassium hydroxide in 400 ml of methanol and 500 ml of dimethyl sulphoxide in the course of one hour. After removal of the methanol on a rotary evaporator, 213 g of methyl iodide, dissolved in 100 ml of dimethyl sulphoxide, are added dropwise, while cooling with ice, and the reaction mixture is stirred at 20° C. for 15 hours and subjected to steam distillation. The distillate is extracted continuously in the extractor with methylene chloride and the extract is concentrated. 85 g (56% of theory) of 5-methoxy-2-methylpyridine are obtained as a colourless oil.

Workup

  1. customAfter removal of the methanol
  2. customon a rotary evaporator, 213 g of methyl iodide
  3. dissolutiondissolved in 100 ml of dimethyl sulphoxide
  4. additionare added dropwise
  5. temperaturewhile cooling with ice
  6. distillationsubjected to steam distillation
  7. extractionThe distillate is extracted continuously in the extractor with methylene chloride
  8. concentrationthe extract is concentrated

Sources & evidence

ORD record
ord-6c26ef79c3734661a4290cb07892fd55
Source dataset
uspto-grants-1987_08
Patent number
US04686230

Reaction notes

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