Methanol → 4-(Dimethoxymethyl)pyridine

HRID 659947Notes

Reaction equation

HRID 659947 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH3:14][O-:15].[Na+].[CH3:17]O>>[CH3:17][O:8][CH:7]([O:15][CH3:14])[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 133894-PyridinecarboxaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 6428534-(Dimethoxymethyl)pyridine

Procedure

80 g (74.6 mmoles) of pyridine-4-carboxaldehyde is dissolved in 150 mL of methanol. 123.5 mL (112 mmoles) of trimethyl orthoformiate is added to the reaction mixture at room temperature followed by the addition of 33 mL of concentrated sulfuric acid. The reaction mixture is kept under reflux for 24 hours and once cooled, added to 300 mL of sodium methylate solution. The white suspension obtained is filtered over celite, the filtrate is concentrated under vacuum and 70.3 g of 4-dimethoxymethyl-pyridine is obtained as a yellow oil.

Workup

  1. addition123.5 mL (112 mmoles) of trimethyl orthoformiate is added to the reaction mixture at room temperature
  2. temperatureunder reflux for 24 hours
  3. temperatureonce cooled
  4. customThe white suspension obtained
  5. filtrationis filtered over celite
  6. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-9ea4c54721df4e6aa19ec0d4659fe814
Source dataset
uspto-grants-2011_12
Patent number
US08084395B2

Reaction notes

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