Water → 2,4-Bis(4-chlorophenyl)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol

HRID 1380918Notes

Reaction equation

HRID 1380918 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:11]([CH3:21])([CH3:20])[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.[Na].O>C(O)CC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:9])([C:11]([CH3:21])([CH3:20])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[CH2:10][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 132174072-(4-Chlorophenyl)-2-[1-(4-chlorophenyl)-2-methylpropan-2-yl]oxiraneHCID 57373095Imidazole sodium

Product 1

HCID 132174082,4-Bis(4-chlorophenyl)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-olYield 35%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Procedure

30 g (0.935 mol) of 2-(4-chlorophenyl)-2-(4-chlorophenyl-tert.-butyl)-oxirane in 40 ml of n-propanol are added dropwise to a solution of 7.7 g (0.108 mol) of sodium imidazole in 60 ml of n-propanol at the reflux temperature. The reaction mixture is subsequently stirred under reflux for 48 hours and cooled, water is added and the mixture is extracted with methylene chloride. The organic phase is dried over sodium sulphate and concentrated in vacuo. The oily residue is stirred into diisopropyl ether. The resulting crystalline precipitate is filtered off with suction and dried. 12.7 g (35% of theory) of 2,4-bis-(4-chlorophenyl)-3,3-dimethyl-1-(imidazol-1-yl)-2-butanol of melting point 174° C. are obtained.

Workup

  1. temperatureunder reflux 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. concentrationconcentrated in vacuo
  6. stirringThe oily residue is stirred into diisopropyl ether
  7. filtrationThe resulting crystalline precipitate is filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-109b8bcdcc524236bd294efce76f766e
Source dataset
uspto-grants-1986_04
Patent number
US04584308

Reaction notes

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