Formaldehyde → HCID 20568527, compound

HRID 1578320Notes

Reaction equation

HRID 1578320 reaction equation
[C:1]1([N:7]2[C:11]([C:12](OCC)=[O:13])=[CH:10][N:9]=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].C=O>O>[C:1]1([N:7]2[C:11]([CH2:12][OH:13])=[CH:10][N:9]=[CH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 14497627HCID 14497627, compound

Product 1

HCID 20568527HCID 20568527, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 2.16 g (0.01 mol) of 1-phenyl-5-carbethoxyimidazole in 5 ml of water are added 0.8 g (0.02 mol) of sodium hydroxide and then 4 ml of ~37% aqueous formaldehyde. The mixture is heated at 80°-90° C. for 2 hours. The reaction mixture is concentrated in vacuo, and then the residue is extracted with ethyl acetate. The ethyl acetate extract is concentrated to give 1-phenyl-5-hydroxymethylimidazole as a solid, m.p. 81°-84° C.

Workup

  1. temperatureThe mixture is heated at 80°-90° C. for 2 hours
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. extractionthe residue is extracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. concentrationis concentrated

Sources & evidence

ORD record
ord-aebafcffb1064f5b815ec4a5a7d91d99
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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