4-Chlorophenol → HCID 13254745, compound

HRID 2291715Notes

Reaction equation

HRID 2291715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Na].[CH3:10][O:11][CH2:12][C:13]([C:16]1([CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)[CH2:18][O:17]1)([CH3:15])[CH3:14]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:16]([OH:17])([C:13]([CH3:15])([CH3:14])[CH2:12][O:11][CH3:10])[CH2:19][N:20]2[CH:24]=[N:23][CH:22]=[N:21]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 5360545SodiumHCID 132547402-(Methoxy-tert.-butyl)-2-(1,2,4-triazol-1-yl-methyl)-oxirane

Product 1

HCID 13254745HCID 13254745, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

8.1 g (0.0633 mol) of 4-chlorophenol were added to a solution of 0.32 g (0.014 mol) of sodium in 100 ml of absolute ethanol. 10.3 g (0.0488 mol) of 2-(methoxy-tert.-butyl)-2-(1,2,4-triazol-1-yl-methyl)-oxirane, dissolve in 300 ml of absolute ethanol, were added, and the reaction mixture was heated under reflux for 48 hours. The reaction mixture was allowed to cool and was concentrated. The residue was taken up in ethyl acetate, and the solution was washed once with water, once with 1N sodium hydroxide solution, again with water, thereafter with 1N hydrochloric acid and 1N sodium hydroxide solution, again with water, and finally with saturated sodium chloride solution. The organic phase was dried over sodium sulphate, and concentrated. 10.7 g (64.6% of theory) of 2-(4-chlorophenoxymethyl)-3,3-dimethyl-4-methoxy-1-(1,2,4-triazol-1-yl)-butan-2-ol of refractive index nD20 =1.531 were obtained.

Workup

  1. additionwere added
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 48 hours
  4. temperatureto cool
  5. concentrationwas concentrated
  6. washthe solution was washed once with water, once with 1N sodium hydroxide solution, again with water
  7. dry with materialThe organic phase was dried over sodium sulphate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fe7ae77932944af1ba22b44353aafca2
Source dataset
uspto-grants-1989_01
Patent number
US04797499

Reaction notes

Loading…