Formaldehyde → (1,5-Dimethyl-1H-imidazol-4-yl)methanol

HRID 1578313Notes

Reaction equation

HRID 1578313 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8](O)=[O:9])[N:4]=[CH:3]1.[OH-].[K+].C=O>>[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH2:8][OH:9])[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 14797Potassium HydroxideHCID 185218601,5-Dimethyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 12373005(1,5-Dimethyl-1H-imidazol-4-yl)methanolYield 70%

Procedure

A mixture of 1,5-dimethylimidazole-4-carboxylic acid (1.4 g, 0.01 mol), potassium hydroxide (1.12 g, 0.02 mol) and ~37% aqueous formaldehyde solution (3 ml) was heated at 80°-90° C. for 3 hours. After completion of the reaction, the solvent was stripped off in vacuo, and the residue was extracted with isopropanol (40 ml). The isopropanol extract was concentrated to give a crude product. The crude solid was recrystallized from acetone and filtered to afford 0.88 g of 1,5-dimethyl-4-hydroxymethylimidazole as a white crystal, m.p. 161°-163° C. Yield 70%.

Workup

  1. temperaturewas heated at 80°-90° C. for 3 hours
  2. customAfter completion of the reaction
  3. extractionthe residue was extracted with isopropanol (40 ml)
  4. extractionThe isopropanol extract
  5. concentrationwas concentrated
  6. customto give a crude product
  7. customThe crude solid was recrystallized from acetone
  8. filtrationfiltered

Sources & evidence

ORD record
ord-00eb5e44b8ea4270a2834847d78c64f2
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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