[C:1]1([CH3:12])[CH:6]=[CH:5][C:4]([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)=[CH:3][CH:2]=1.C=O.[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21][O:22]CCO>O>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([C:7]2[NH:11][C:10]([CH2:15][OH:18])=[C:9]([CH2:21][OH:22])[N:8]=2)=[CH:5][CH:6]=1A mixture of 15.8 g (0.1 mole) of 2-p-tolyl imidazole, 9 g (0.3 mole) of paraformaldehyde, 2 g (0.015 mole) of potassium carbonate, and 50 ml of methyl cellosolve was heated at 95° C. for 30 minutes with stirring in the same way as in Example 1. 200 ml of water was added, and the reaction mixture was boiled for a while and cooled. The crystals were collected by filtration, boiled together with 20 ml of toluene, and cooled. The crystals were collected by filtration and recrystallized from methyl cellosolve to afford 2-p-tolyl-4,5-dihydroxymethyl imidazole as a final product in an amount of 4.5 g (yield 21%). The thin-layer chromatography (cellulose:n-BuOH:AcOH:W = 4:1:2) of the crystals gave only one spot at Rf = 0.73.
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