Formaldehyde → 4-(1-Methylethyl)-1H-imidazole-5-methanol

HRID 1578314Notes

Reaction equation

HRID 1578314 reaction equation
[CH:1]([C:4]1[N:5]=[CH:6][NH:7][C:8]=1[C:9](O)=[O:10])([CH3:3])[CH3:2].[O-2].[Ca+2].C=O>>[CH:1]([C:4]1[N:5]=[CH:6][NH:7][C:8]=1[CH2:9][OH:10])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 6850728CalciumoxideHCID 178440196HCID 178440196, compound

Product 1

HCID 126154624-(1-Methylethyl)-1H-imidazole-5-methanol

Procedure

A mixture of 4-isopropylimidazole-5-carboxylic acid (1.54 g, 0.01 mol), calcium oxide (0.56 g, 0.01 mol) and ~37% aqueous formaldehyde solution (4 ml) is heated at 70°-80° C. for 3 hours, with stirring. After completion of the reaction, the solvent is stripped off, and the residue is extracted with acetone. The acetone extract is concentrated, and the resultant residue is recrystallized from ethyl acetate and filtered to give 4-isopropyl-5-hydroxymethylimidazole as a solid, m.p. 125°-127° C.

Workup

  1. temperatureis heated at 70°-80° C. for 3 hours
  2. customAfter completion of the reaction
  3. extractionthe residue is extracted with acetone
  4. extractionThe acetone extract
  5. concentrationis concentrated
  6. customthe resultant residue is recrystallized from ethyl acetate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-47ff0785a27740b8aafea4db184b6631
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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