4-Fluorophenol → HCID 23042740, compound

HRID 2165505Notes

Reaction equation

HRID 2165505 reaction equation
[C:1]([C:5]1([CH:8]([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH3:9])[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1>COCCOCCOC.O.[OH-].[Li+]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:7][C:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([OH:6])[CH:8]([CH3:9])[N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 97324-FluorophenolHCID 23042747HCID 23042747, compound

Product 1

HCID 23042740HCID 23042740, compoundYield 69.9%

Reagents, catalysts & solvents 2

HCID 168937Lithium hydroxide, monohydrateCatalystHCID 8150DiglymeSolvent

Procedure

A mixture of 10.0 g of 2-tert-butyl-2-[1-(1H-1,2,4-triazol-1-yl)ethyl]-oxirane, 6.4 g of 4-fluorophenol and 0.1 g of lithium hydroxide hydrate in 10 ml of diethylene glycol dimethyl ether is heated for 18 hours to 150° C. After it has cooled, the reaction mixture is poured into ice-water and extracted with ether. The organic phase is washed with water and a saturated solution of sodium chloride, dried and concentrated. Chromatography over silica gel with a 3:1 mixture of ethyl acetate/toluene as eluant yields 11.0 g of 1-(4-fluorophenoxy)-2-tert-butyl-2-hydroxy-3-methyl-3-(1H-1,2,4-triazol-1-yl)propane with a melting point of 85°-100° C. (compound 18).

Workup

  1. temperatureis heated for 18 hours to 150° C
  2. temperatureAfter it has cooled
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. dry with materiala saturated solution of sodium chloride, dried
  6. concentrationconcentrated
  7. additionChromatography over silica gel with a 3:1 mixture of ethyl acetate/toluene as eluant

Sources & evidence

ORD record
ord-8f78798f60824966960673fef6fe9e90
Source dataset
uspto-grants-1990_07
Patent number
US04940481

Reaction notes

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