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

HRID 1462860Notes

Reaction equation

HRID 1462860 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-].[K+]>CO>[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

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 13336817HCID 13336817, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (+)-3-[2-(4-chlorophenyl)isovaleroyloxy]-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (2.89 g; M.P., 145°-146.5° C.) in methanol (40 ml) was added a 20% aqueous potassium hydroxide solution (6 ml), and the mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo, and the oily residue was dissolved in 6N hydrochloric acid (30 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, 1.51 g; 81%. M.P., 143° C. [α]D19, -113.1° (C=1.0, MeOH).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe oily residue was dissolved in 6N hydrochloric acid (30 ml)
  3. washThe acidic aqueous solution was washed with chloroform (20 ml×2)
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c7c20649aa3f42408ff0d8190de18e46
Source dataset
uspto-grants-1984_07
Patent number
US04461774

Reaction notes

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