Hydrochloric Acid → 4-Hydroxymethyl-2-p-methoxyphenyl-5-methyl-imidazole hydrochloride

HRID 839126Notes

Reaction equation

HRID 839126 reaction equation
[ClH:1].C([O:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12])(C)C.Cl>O>[ClH:1].[OH:5][CH2:6][C:7]1[N:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[NH:10][C:11]=1[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 203258814-Isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride

Product 1

HCID 203258964-Hydroxymethyl-2-p-methoxyphenyl-5-methyl-imidazole hydrochlorideYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-isopropoxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride (48.9 g, 0.164 mole) in 500 ml of water is stirred and refluxed. To this mixture is added 50 ml of concentrated hydrochloric acid and stirring and refluxing are continued for 4 hrs. The mixture is then chilled and filtered to give about 39.5 g (94%) of 4-hydroxymethyl-2-(p-methoxyphenyl)-5-methylimidazole hydrochloride which is recrystallized from isopropyl alcohol, m.p. 146°-148° C (dec.). Treatment with alkali (e.g., NaOH) affords the corresponding base form.

Workup

  1. temperaturerefluxed
  2. stirringstirring
  3. temperaturerefluxing
  4. temperatureThe mixture is then chilled
  5. filtrationfiltered

Sources & evidence

ORD record
ord-87b5c2953a6b4bae8a0da0c78ec64c46
Source dataset
uspto-grants-1978_06
Patent number
US04093811

Reaction notes

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