Formaldehyde → (1-Cyclohexyl-1H-imidazol-5-yl)methanol

HRID 1578318Notes

Reaction equation

HRID 1578318 reaction equation
[CH:1]1([N:7]2[C:11]([C:12](OC)=[O:13])=[CH:10][N:9]=[CH:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].C=O>O>[CH:1]1([N:7]2[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[CH:8]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 14497626Methyl 1-cyclohexyl-1H-imidazole-5-carboxylate

Product 1

HCID 20568533(1-Cyclohexyl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2.1 g (0.01 mol) of 1-cyclohexyl-5-carbmethoxyimidazole in 6 ml of water are added 0.8 g (0.02 mol) of sodium hydroxide and 4 ml of ~37% aqueous formaldehyde solution. The resultant mixture is heated at 80°-90° C. for about 2 hours. After completion of the reaction, the solvent is stripped off, and the remaining residue is extracted with ethyl acetate. The ethyl acetate extracted is concentrated to give 1-cyclohexyl-5-hydroxymethylimidazole as a solid, m.p. 133°-134° C.

Workup

  1. customAfter completion of the reaction
  2. extractionthe remaining residue is extracted with ethyl acetate
  3. extractionThe ethyl acetate extracted
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-700a4654e6754c1ba1cbb0c305c4df17
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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