Hydrochloric Acid → 1,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol

HRID 1995922Notes

Reaction equation

HRID 1995922 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH:7]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[C:8](=[O:21])[C:9]([CH3:20])([CH3:19])[CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH:8]([OH:21])[C:9]([CH3:19])([CH3:20])[CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 127659761,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one

Product 1

HCID 127660001,4-Bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-olYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

13.1 g (0.031 mol) of 1,4-bis-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-one (Example 2) were dissolved in 100 ml of methanol, and 1.4 g of sodium borohydride were added in portions at 0° to 5° C. The mixture was subsequently stirred at room temperature for 5 hours, acidified with 10 ml of 2 N hydrochloric acid and stirred at room temperature for a further 2 hours. The solvent was then distilled off in vacuo and the residue was taken up in 300 ml of methylene chloride. The mixture was stirred with 200 ml of saturated sodium bicarbonate solution, the organic phase was separated off, washed twice with 300 ml of water each time and dried over sodium sulphate and the solvent was distilled off in vacuo. The colorless residue was taken up in 50 ml of diisopropyl ether and the crystals formed were filtered off. 10.8 g (82.7% of theory) of 1,4-bis-(4-chlorophenoxy)-3,3 -dimethyl-1-(imidazol-1-yl)-butan-2-ol were obtained as a diastereomer mixture of melting point 142°-144° C.

Workup

  1. stirringstirred at room temperature for a further 2 hours
  2. distillationThe solvent was then distilled off in vacuo
  3. stirringThe mixture was stirred with 200 ml of saturated sodium bicarbonate solution
  4. customthe organic phase was separated off
  5. washwashed twice with 300 ml of water each time
  6. dry with materialdried over sodium sulphate
  7. distillationthe solvent was distilled off in vacuo
  8. customthe crystals formed
  9. filtrationwere filtered off

Sources & evidence

ORD record
ord-cbf8add07fa44195bceb8ae561b6acad
Source dataset
uspto-grants-1983_09
Patent number
US04406909

Reaction notes

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