Acetic Acid → 3-Hydroxypyridine-2,6-dimethanol

HRID 2386206Notes

Reaction equation

HRID 2386206 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]=[O:9].C[C:11]([OH:13])=O>[OH-].[Na+]>[OH:1][C:2]1[C:3]([CH2:11][OH:13])=[N:4][C:5]([CH2:8][OH:9])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 79713-Hydroxypyridine

Product 1

HCID 4173663-Hydroxypyridine-2,6-dimethanol

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

71.1 g (0.75 mol) of 3-hydroxypyridine are dissolved in 300 ml of a 10% aqueous NaOH solution. The combined mixture is brought to 90° C. and then 7×60 ml of a 30% formaldehyde solution are introduced portionwise (5.1 mol). The mixture is left at ambient temperature overnight and then neutralized with CH3COOH. It is concentrated and the residue is taken up in 600 ml of DMF. The insoluble light material is separated. The liquors are acidified with 75 ml 10N HCl. The mixture is concentrated. The residual oil is purified by chromatography on silanized silica with elution with water. Crystals are obtained. w=47 g.

Workup

  1. customis brought to 90° C.
  2. concentrationIt is concentrated
  3. customThe insoluble light material is separated
  4. concentrationThe mixture is concentrated
  5. customThe residual oil is purified by chromatography on silanized silica with elution with water
  6. customCrystals are obtained

Sources & evidence

ORD record
ord-3447fbbd16d54f95a3c3cec94eb3b942
Source dataset
uspto-grants-2012_09
Patent number
US08268810B2

Reaction notes

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