Formaldehyde → [2-(3-Methylphenyl)-1H-imidazole-4,5-diyl]dimethanol

HRID 1112483Notes

Reaction equation

HRID 1112483 reaction equation
[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:2]=1.[CH2:13]=[O:14].[C:15](=[O:18])([O-])[O-].[K+].[K+]>>[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:11][C:10]([CH2:15][OH:18])=[C:9]([CH2:13][OH:14])[N:8]=2)[CH:2]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 126227242-(3-Methylphenyl)-1H-imidazole

Product 1

HCID 22764400[2-(3-Methylphenyl)-1H-imidazole-4,5-diyl]dimethanolYield 9%

Conditions

Temperature
90 °C

Procedure

A reaction vessel equipped with a stirrer and a reflux condenser was charged with 15.8 g (0.1 mole) of 2-m-tolylimidazole, 24 ml (0.3 mole) of 37% formalin and 2 g (0.015 mole) of potassium carbonate. They were heated at about 90° C. for 1 hour with stirring. The contents were cooled, and the crystals were collected by filtration. The crystals collected were boiled together with 50 ml of water, cooled, and again collected by filtration. The crystals so collected were then boiled together with 20 ml of toluene, cooled, and collected by filtration. The crystals were recrystallized from methanol to afford 2-m-tolyl-4,5-dihydroxymethyl imidazole as a final product in an amount of 2 g (yield 9%). The thin-layer chromatography (Alumina G, ethanol) of these crystals gave only one spot at Rf = 0.7.

Workup

  1. customA reaction vessel equipped with a stirrer and a reflux condenser
  2. temperatureThe contents were cooled
  3. filtrationthe crystals were collected by filtration
  4. customThe crystals collected
  5. temperaturecooled
  6. filtrationagain collected by filtration
  7. customThe crystals so collected
  8. temperaturecooled
  9. filtrationcollected by filtration
  10. customThe crystals were recrystallized from methanol

Sources & evidence

ORD record
ord-c83c1b106c6b4ee888279b573f0cb9ec
Source dataset
uspto-grants-1978_10
Patent number
US04122277

Reaction notes

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