Formaldehyde → 6-(Hydroxymethyl)-2-methylpyridin-3-ol

HRID 1606307Notes

Reaction equation

HRID 1606307 reaction equation
[OH:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[OH-:9].[Na+].O.[CH2:12]=O>C(O)(=O)C>[OH:1][C:2]1[C:3]([CH3:8])=[N:4][C:5]([CH2:12][OH:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 712Formaldehyde2×HCID 962WaterHCID 14798Sodium HydroxideHCID 707192-Methylpyridin-3-ol

Product 1

HCID 123972606-(Hydroxymethyl)-2-methylpyridin-3-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 27.2 g. (0.25 mol) of 3-hydroxy-2-methylpyridine, 100 ml. of 10% sodium hydroxide in 75 ml. of water and 22.5 ml. (0.25 mol) of 40% formalin (aqueous methanolic formaldehyde solution) is refluxed for two hours. An additional amount of 40% formalin (22.5 ml.) is added and the reflux is continued for two hours. The mixture is acidified with acetic acid and the resulting precipitate is filtered and washed with acetone. The filtrate is evaporated to dryness and the residue is repeatedly extracted with hot acetone. The extract is dried, treated with charcoal and evaporated to give crude 3-hydroxy-6-hydroxymethyl-2-methylpyridine as a solid.

Workup

  1. additionA mixture of 27.2 g
  2. filtrationthe resulting precipitate is filtered
  3. washwashed with acetone
  4. customThe filtrate is evaporated to dryness
  5. extractionthe residue is repeatedly extracted with hot acetone
  6. customThe extract is dried
  7. additiontreated with charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-c2ac2dd992a4428c984cfc99a93c0289
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

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