Hydrochloric Acid → HCID 12766922, compound

HRID 262155Notes

Reaction equation

HRID 262155 reaction equation
[N:1]1([CH:6]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[N:1]1([CH:6]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:7]([OH:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 13021672HCID 13021672, compound

Product 1

HCID 12766922HCID 12766922, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25.8 g (0.1 mol) of 1-imidazol-1-yl-1-phenoxy-3,3-dimethyl-butan-2-one are dissolved in 250 ml of methanol and 5.9 g (0.15 mol) of sodium borohydride are introduced in portions into this solution, at 5° to 10° C., while stirring and with reflux cooling. After stirring for 15 hours at room temperature, 20 ml of concentrated hydrochloric acid are added and the reaction mixture is stirred for a further 15 hours at room temperature and poured into 300 ml of saturated sodium bicarbonate solution. The mixture is extracted with twice 100 ml of methylene chloride, the organic phase is washed with twice 100 ml of water and dried over sodium sulphate and the solvent is distilled off under a water pump vacuum. The residue is ground with 30 ml of petroleum ether. 21.6 g (83% of theory) of 1-imidazol-1-yl-1-phenoxy-3,3-dimethyl-butan-2-ol are obtained as a mixture of isomers with a melting point of 99°-105° C.

Workup

  1. temperaturewith reflux
  2. temperaturecooling
  3. stirringAfter stirring for 15 hours at room temperature
  4. stirringthe reaction mixture is stirred for a further 15 hours at room temperature
  5. extractionThe mixture is extracted with twice 100 ml of methylene chloride
  6. washthe organic phase is washed with twice 100 ml of water
  7. dry with materialdried over sodium sulphate
  8. distillationthe solvent is distilled off under a water pump vacuum

Sources & evidence

ORD record
ord-713908196bcc49a78b064dc44af46979
Source dataset
uspto-grants-1979_05
Patent number
US04153708

Reaction notes

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