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

HRID 2419117Notes

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

Reactant 3

HCID 712Formaldehyde

HCID 11430Potassium Carbonate

HCID 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

customA reaction vessel equipped with a stirrer and a reflux condenser
temperatureThe contents were cooled
filtrationthe crystals were collected by filtration
customThe crystals collected
temperaturecooled
filtrationagain collected by filtration
customThe crystals so collected
temperaturecooled
filtrationcollected by filtration
customThe crystals were recrystallized from methanol

Sources & evidence

ORD record: ord-d6bb02576d144f90a82e5b6d8e79d298
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04104473

Reaction notes

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