Acetic Acid → alpha-Phenyl-alpha-(p-trifluoromethylphenyl)imidazole-2-methanol

HRID 261948Notes

Reaction equation

HRID 261948 reaction equation
COC[N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=1)[OH:10].C(O)(=O)C.Cl>O>[C:21]1([C:9]([C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)([C:5]2[NH:4][CH:8]=[CH:7][N:6]=2)[OH:10])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 124338961-(Methoxymethyl)-alpha-phenyl-alpha-(p-trifluoromethyl-phenyl)imidazole-2-methanol

Product 1

HCID 12433853alpha-Phenyl-alpha-(p-trifluoromethylphenyl)imidazole-2-methanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9 g. (0.025 mol) of 1-(methoxymethyl)-α-phenyl-α-(p-trifluoromethyl-phenyl)imidazole-2-methanol, 70 ml. of glacial acetic acid, 7 ml. of concentrated hydrochloric acid and 7 ml. of water was refluxed for 3.5 hours. After cooling, the liquid was distilled off and 2 N sodium hydroxide solution and a small amount of ethanol were added to the residue. The alcohol was distilled off and the aqueous phase was extracted with diethyl ether. The ethereal solution was washed with water and dried over sodium sulphate and the solvent was distilled off. The residue was first crystallised from a mixture of toluene and petroleum ether (boiling range 40°-60° C.) and subsequently from isopropyl alcohol. α-Phenyl-α-(p-trifluoromethylphenyl)imidazole-2-methanol was obtained. Melting point 174°-175.5° C.

Workup

  1. additionA mixture of 9 g
  2. temperatureAfter cooling
  3. distillationthe liquid was distilled off
  4. addition2 N sodium hydroxide solution and a small amount of ethanol were added to the residue
  5. distillationThe alcohol was distilled off
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. washThe ethereal solution was washed with water
  8. dry with materialdried over sodium sulphate
  9. distillationthe solvent was distilled off
  10. customThe residue was first crystallised from a mixture of toluene and petroleum ether (boiling range 40°-60° C.) and subsequently from isopropyl alcohol

Sources & evidence

ORD record
ord-1f80f93d79a8410a8a6b694a39fa17a8
Source dataset
uspto-grants-1979_05
Patent number
US04152441

Reaction notes

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