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Sodium Hydroxide → 2-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol

HRID 1462859
Notes
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Reaction equation

HRID 1462859 reaction equation
ClC1C=CC(C(C(C)C)C([O:11][CH2:12][C:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])([OH:20])[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=O)=CC=1.[OH-].[Na+]>C(O)C.O>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:13]([OH:20])([CH2:12][OH:11])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13336817HCID 13336817, compound

Product 1

HCID 133368182-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (-)-3-[2-(4-chlorophenyl)isovaleroyloxy]-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (6.85 g; M.P., 174°-175° C.) in ethanol (60 ml) was added a solution of sodium hydroxide (1.8 g) in water (10 ml), and the mixture was heated with stirring at 80° C. for 4 hours. The solvent was removed in vacuo and the residue was dissolved in 6N hydrochloric acid (70 ml). The acidic aqueous solution was washed with chloroform (20 ml×2) and then neutralized with a 28% aqueous ammonia solution. The resulting crystals were collected by filtration to give (-)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2,3-propanediol. Yield, 3.6 g; 88%. M.P., 138.5°-141° C. [α]D24, -108.5° (C=1.0, MeOH).

Workup

  1. temperaturethe mixture was heated
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 6N hydrochloric acid (70 ml)
  4. washThe acidic aqueous solution was washed with chloroform (20 ml×2)
  5. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-2780288329b442eab08de2810c497fcf
Source dataset
uspto-grants-1984_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04461774

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes