Sodium Bicarbonate → 4-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol

HRID 126880Notes

Reaction equation

HRID 126880 reaction equation
C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1.[Cl:19][C:20]1[CH:39]=[CH:38][C:23]([O:24][CH:25]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[C:26](=[O:32])[C:27]([CH3:31])([CH3:30])[CH2:28][Cl:29])=[CH:22][CH:21]=1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>C(Cl)Cl.C(O)(C)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH:25]([N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)[CH:26]([OH:32])[C:27]([CH3:30])([CH3:31])[CH2:28][Cl:29])=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20286585HCID 20286585, compound

Product 1

HCID 202865634-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-olYield 75%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

18.8 g (0.04 mol) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-one naphthalene-1,5-disulphonate were suspended in 100 ml of methylene chloride, and 100 ml of sodium bicarbonate solution were added. The organic phase was separated off, dried over sodium sulphate and concentrated by distilling off the solvent in vacuo. The base thus obtained was taken up in 100 ml of isopropanol, and 2 g (0.05 mol) of sodium borohydride were added in portions at 5° to 10° C. The mixture was stirred at room temperature for 15 hours and the isopropanol was then distilled off. The residue was taken up in 100 ml of methylene chloride and, after adding 100 ml of water, the mixture was stirred at room temperature for a further 15 hours. The organic phase was then separated off, washed twice with 50 ml of water each time, dried over sodium sulphate and concentrated. The oil which remained was boiled up in 100 ml of petroleum ether, whereupon crystallization occurred. 9.8 g (75% of theory) of 1-(4-chlorophenoxy)-1-(imidazol-1-yl)-3,3-dimethyl-4-chloro-butan-2-ol of melting point 120°-125° C. were obtained. ##STR15##

Workup

  1. customThe organic phase was separated off
  2. dry with materialdried over sodium sulphate
  3. concentrationconcentrated
  4. distillationby distilling off the solvent in vacuo
  5. customThe base thus obtained
  6. distillationthe isopropanol was then distilled off
  7. additionafter adding 100 ml of water
  8. stirringthe mixture was stirred at room temperature for a further 15 hours
  9. customThe organic phase was then separated off
  10. washwashed twice with 50 ml of water each time
  11. dry with materialdried over sodium sulphate
  12. concentrationconcentrated
  13. customThe oil which remained was boiled up in 100 ml of petroleum ether, whereupon crystallization

Sources & evidence

ORD record
ord-c861772bef124816842f6f9cad1722f4
Source dataset
uspto-grants-1981_03
Patent number
US04254132

Reaction notes

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