Sodium Methoxide → HCID 21490891, compound

HRID 1973894Notes

Reaction equation

HRID 1973894 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:5]([Cl:14])[N:4]=1.[CH3:15][O-:16].[Na+]>CO>[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[C:6]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:5]([O:16][CH3:15])[N:4]=1.[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:16][CH3:15])[C:6]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:5]([Cl:14])[N:4]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 21490887HCID 21490887, compound

Product 2

HCID 21490891HCID 21490891, compoundHCID 21490913HCID 21490913, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 103 g (0.44 mol) of 2-hydroxymethyl-4,6dichloro-5-n-butyl-pyridine in 100 ml of methanol is added dropwise over the course of 15 minutes, whilst stirring, to a solution of 59.4 g (1.1 mol) of sodium methylate in 500 ml of methanol. After completion of the addition, the reaction mixture is heated for 56 hours under reflux. It is then evaporated to dryness and the residue is suspended in ether. After filtration, the ether filtrate is dried by means of sodium sulphate, filtered and evaporated. Fractional distillation of the residue in a high vacuum yields 2-hydroxymethyl-4-chloro-5-n-butyl-6-methoxy-pyridine of the formula ##STR10## of boiling point 95°-98° (0.06 mm Hg) and 2-hydroxymethyl-4-methoxy-5-n-butyl-6-chloro-pyridine of the formula ##STR11## of boiling point 130°-134° (0.03 mm Hg).

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture is heated for 56 hours
  3. temperatureunder reflux
  4. customIt is then evaporated to dryness
  5. filtrationAfter filtration
  6. dry with materialthe ether filtrate is dried by means of sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. distillationFractional distillation of the residue in a high vacuum

Sources & evidence

ORD record
ord-bf8d8e5d0da84eb097b47a79715baaec
Source dataset
uspto-grants-1976_12
Patent number
US03998955

Reaction notes

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