Formaldehyde → (1-(propan-2-yl)-1H-imidazol-5-yl)methanol

HRID 1578317Notes

Reaction equation

HRID 1578317 reaction equation
[CH:1]([N:4]1[C:8]([C:9](OC)=[O:10])=[CH:7][N:6]=[CH:5]1)([CH3:3])[CH3:2].[OH-].[Na+].C=O>O>[CH:1]([N:4]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[CH:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 14497625Methyl 1-(1-methylethyl)-1H-imidazole-5-carboxylate

Product 1

HCID 20568531(1-(propan-2-yl)-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.68 g (0.01 mol) of 1-isopropyl-5-carbmethoxyimidazole is suspended in 5 ml of water. To the suspension are added 0.8 g (0.02 mol) of sodium hydroxide and 4 ml of ~37% aqueous formaldehyde. The resultant mixture is heated to reflux for 2 hours. After completion of the reaction, the solvent is stripped off, and the residue is extracted with ethyl acetate and concentrated to give 1-isopropyl-5-hydroxymethylimidazole as a solid, m.p. 83°-84° C.

Workup

  1. temperatureto reflux for 2 hours
  2. customAfter completion of the reaction
  3. extractionthe residue is extracted with ethyl acetate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cc3f4e498c0f4806bdb4cb2e6c05c24c
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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