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

HRID 1112485Notes

Reaction equation

HRID 1112485 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.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]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 5940452-(4-Methylphenyl)-1H-imidazole

Product 1

HCID 22764401[2-(4-Methylphenyl)-1H-imidazole-4,5-diyl]dimethanolYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A 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.

Workup

  1. temperaturecooled
  2. filtrationThe crystals were collected by filtration
  3. temperaturecooled
  4. filtrationThe crystals were collected by filtration
  5. customrecrystallized from methyl cellosolve

Sources & evidence

ORD record
ord-5fe197ff8e0e4e6a8ba90d799d6688ac
Source dataset
uspto-grants-1978_10
Patent number
US04122277

Reaction notes

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