1H-1,2,4-Triazole → 2-(4-Chlorophenoxymethyl)-1-(1,2,4-triazol-1-yl)-3,3,4-trimethylpentan-2-ol

HRID 1087698Notes

Reaction equation

HRID 1087698 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]2([C:11]([CH3:16])([CH3:15])[CH:12]([CH3:14])[CH3:13])[CH2:10][O:9]2)=[CH:4][CH:3]=1.C([O-])CCC.[Na+].[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1>C(O)CCC>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]([OH:9])([C:11]([CH3:16])([CH3:15])[CH:12]([CH3:14])[CH3:13])[CH2:10][N:25]2[CH:29]=[N:28][CH:27]=[N:26]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 221632272-(4-Chlorophenoxymethyl)-2-(1,1,2-trimethylpropyl)-oxiraneHCID 23669364Sodium n-butylate

Product 1

HCID 143285852-(4-Chlorophenoxymethyl)-1-(1,2,4-triazol-1-yl)-3,3,4-trimethylpentan-2-olYield 36.8%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

376 g of crude 2-(4-chlorophenoxymethyl)-2-(1,1,2-trimethylpropyl)-oxirane dissolved in 400 ml of n-butanol are added dropwise to a boiling solution of 13.4 g (0.14 mol) of sodium butanolate and 97 g (1.4 mols of 1,2,4-triazole in 400 ml of n-butanol in 1.5 hours. After boiling under reflux for 22 hours, the solvent is removed by distillation under reduced pressure and 500 ml of dichloromethane are added to the residue. Precipitated 2-(4-chlorophenoxymethyl)-1-(1,2,4-triazol-4-yl)-3,3,4-trimethylpentan-2-ol (15 g; melting point 173°-174° C.) is filtered off from the mixture, the filtrate is washed twice with 250 ml of water each time and dried over anhydrous sodium sulphate and the solvent is removed by distillation. The residue is chromatographed on silica gel using trichloromethane as eluant. 174 g of 2-(4-chlorophenoxymethyl)-1-(1,2,4-triazol-1-yl)-3,3,4-trimethylpentan-2-ol are thus obtained in the form of colorless crystals of melting point 59°-60° C.

Workup

  1. temperatureunder reflux for 22 hours
  2. customthe solvent is removed by distillation under reduced pressure and 500 ml of dichloromethane
  3. additionare added to the residue
  4. filtrationPrecipitated 2-(4-chlorophenoxymethyl)-1-(1,2,4-triazol-4-yl)-3,3,4-trimethylpentan-2-ol (15 g; melting point 173°-174° C.) is filtered off from the mixture
  5. washthe filtrate is washed twice with 250 ml of water each time
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent is removed by distillation
  8. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-c0e201cccb794cf1a748d66ff1d24459
Source dataset
uspto-grants-1990_10
Patent number
US04960453

Reaction notes

Loading…