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

HRID 1112484Notes

Reaction equation

HRID 1112484 reaction equation
[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.[CH2:13]=[O:14].[OH-].[K+].[CH3:17][O:18]CCO>>[C:1]1([CH3:12])[CH:2]=[CH:3][C:4]([C:7]2[NH:11][C:10]([CH2:13][OH:14])=[C:9]([CH2:17][OH:18])[N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 712FormaldehydeHCID 80192-MethoxyethanolHCID 14797Potassium HydroxideHCID 5940452-(4-Methylphenyl)-1H-imidazole

Product 1

HCID 22764401[2-(4-Methylphenyl)-1H-imidazole-4,5-diyl]dimethanolYield 9%

Procedure

A mixture of 15.8 g (0.1 mole) of 2-p-tolylimidazole, 24 ml (0.3 mole) of 37% formalin and 2 g of potassium hydroxide was heated for 30 minutes with stirring in the same way as in Example 1, and the reaction mixture was post-treated in the same way as in Example 1 except that methyl cellosolve was used instead of methanol as a recrystallization solvent to afford 2-p-tolyl-4,5-dihydroxymethyl imidazole as a final product in an amount of 2 g (yield 9%).

Workup

  1. temperaturewas heated for 30 minutes

Sources & evidence

ORD record
ord-45c9cfa4d99a44279d462646173246ac
Source dataset
uspto-grants-1978_10
Patent number
US04122277

Reaction notes

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