Sodium Hydroxide → (1,4-dimethyl-1H-imidazol-5-yl)methanol

HRID 1578321Notes

Reaction equation

HRID 1578321 reaction equation
[CH3:1][N:2]1[C:6]([C:7](OCC)=[O:8])=[C:5]([CH3:12])[N:4]=[CH:3]1.[OH-].[Na+].S(=O)(O)[O-].[Na+].C=O>O>[CH3:1][N:2]1[C:6]([CH2:7][OH:8])=[C:5]([CH3:12])[N:4]=[CH:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12685481Ethyl 1,4-dimethyl-1H-imidazole-5-carboxylateHCID 23687474HCID 23687474, compound

Product 1

HCID 20568532(1,4-dimethyl-1H-imidazol-5-yl)methanolYield 36.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1.68 g (0.01 mol) of 1,4-dimethyl-5-carbethoxyimidazole in 10 ml of water was added 0.8 g (0.02 mol) of sodium hydroxide. The mixture was heated to reflux for 30 min. Thereafter, 3.54 g (0.03 mol) of formaldehyde sodium bisulfite was added and heated to reflux for 4 hours. The water in the reaction mixture was removed, and the residue was extracted with isopropyl alcohol and filtered. The isopropyl alcohol extract was concentrated, and the residual solid recrystallized from ethyl acetate and filtered to afford 0.46 g of 1,4-dimethyl-5-hydroxymethylimidazole as a white powdered solid, m.p. 125°-127° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureheated
  4. temperatureto reflux for 4 hours
  5. customThe water in the reaction mixture was removed
  6. extractionthe residue was extracted with isopropyl alcohol
  7. filtrationfiltered
  8. extractionThe isopropyl alcohol extract
  9. concentrationwas concentrated
  10. customthe residual solid recrystallized from ethyl acetate
  11. filtrationfiltered

Sources & evidence

ORD record
ord-7dfad02df0b041c08aaca52f5847e023
Source dataset
uspto-grants-1981_09
Patent number
US04292431

Reaction notes

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