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

HRID 2419120Notes

Reaction equation

[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.C=O.[C:15](=[O:18])([O-])[O-].[K+].[K+].[CH3:21][O:22]CCO>O>[C:1]1([CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][C:10]([CH2:15][OH:18])=[C:9]([CH2:21][OH:22])[N:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 15.8 g (0.1 mole) of 2-o-tolylimidazole 9 g (0.3 mole) of paraformaldehyde, 2 g (0.015 mole) of potassium carbonate and 50 ml of methyl cellosolve was heated at 90° C. for 30 minutes with stirring in the same way as in Example 1. Then, 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 g of toluene, and collected by filtration. The crystals collected were dissolved in acetone, and a small amount of activated carbon was added. The mixture was filtered, and the filtrate was evaporated to dryness to afford 2-o-tolyl-4,5-dihydroxymethyl imidazole as a final product in an amount of 1 g (yield 5%). The thin-layer chromatography (alumina G, ethanol) of the crystals gave only one spot at Rf = 0.6-0.8.

Workup

temperaturecooled
filtrationThe crystals were collected by filtration
filtrationcollected by filtration
customThe crystals collected
dissolutionwere dissolved in acetone
additiona small amount of activated carbon was added
filtrationThe mixture was filtered
customthe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-e0660897e5224688a143d8dee8d7ef64
Source dataset: uspto-grants-1978_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04104473

Reaction notes

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