Water → (2-Phenyl-1H-imidazol-5-yl)methanol

HRID 1578316Notes

Reaction equation

HRID 1578316 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([C:12](O)=[O:13])[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C=O.O1CCOCC1>[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12][OH:13])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 178524792HCID 178524792, compound

Product 1

HCID 10080865(2-Phenyl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 1.88 g (0.01 mol) of 2-phenylimidazole-4-carboxylic acid in a mixture of 3 ml of ~37% formaldehyde and 3 ml of 1,4-dioxane is added 2.1 g (0.02 mol) of sodium carbonate, and the resultant mixture is heated at 60°-70° C. for 5 hours, with stirring. After completion of the reaction, 5 ml of water is added, and the mixture is allowed to stand for 2 hours, on cooling. The resultant solid is recovered by filtration and recrystallized from ethyl acetate and filtered to afford 2-phenyl-4-hydroxymethylimidazole as a solid, m.p.168°-170° C.

Workup

  1. additionis added
  2. temperatureon cooling
  3. filtrationThe resultant solid is recovered by filtration
  4. customrecrystallized from ethyl acetate
  5. filtrationfiltered

Sources & evidence

ORD record
ord-e2db78945aea4502871cfff6e8518116
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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