Water → 3-(4-Chlorophenoxy)-2-(4-chlorophenyl)-3-methyl-1-(1,2,4-triazol-1-yl)-2-butanol

HRID 979452Notes

Reaction equation

HRID 979452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)([CH3:13])[CH3:12])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:22]1[CH:26]=[N:25][CH:24]=[N:23]1.[Na].O>C(O)CC>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:11]([CH3:13])([CH3:12])[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)([OH:9])[CH2:10][N:22]2[CH:26]=[N:25][CH:24]=[N:23]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 198424852-[2-(4-Chlorophenoxy)propan-2-yl]-2-(4-chlorophenyl)oxiraneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 132174093-(4-Chlorophenoxy)-2-(4-chlorophenyl)-3-methyl-1-(1,2,4-triazol-1-yl)-2-butanolYield 18.4%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

A solution of 30 g (0.093 mole) of 2-(4-chlorophenyl)-2-[2-(p-chlorophenoxy)-2-propyl]oxirane in 40 ml of n-propanol is added dropwise, at room temperature, to a solution of 7.6 g (0.107 mole) of 1,2,4-triazole-sodium in 60 ml of n-propanol. The reaction mixture is allowed to stir at reflux temperature for 48 hours, then cooled, water is added and the mixture is extracted with methylene chloride. The organic phase is dried over sodium sulphate and evaporated in vacuo. The oily residue is purified by column chromatography. 6.7 g (18.4% of theory) of 3-(4-chlorophenoxy)-2-(4-chlorophenyl)-3-methyl-1-(1,2,4-triazol-1-yl)-2-butanol are obtained. This is vigorously stirred with 20 ml of saturated hydrogen chloride/ether solution at room temperature. The precipitate which separates out is filtered off with suction, washed with a little ether and dried in vacuo at 40° C. 6.5 g (89% of theory relative to base employed) of 3 -(4-chlorophenoxy)-2-(4-chlorophenyl)-3-methyl-1-(1,2,4-triazol-1-yl)-2-butanol hydrochloride of melting point 135° C. are obtained.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. temperaturecooled
  3. extractionthe mixture is extracted with methylene chloride
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. customevaporated in vacuo
  6. customThe oily residue is purified by column chromatography

Sources & evidence

ORD record
ord-f36f9d9c1301434fa83834551cd9e013
Source dataset
uspto-grants-1987_05
Patent number
US04668660

Reaction notes

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