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