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

HRID 1638370Notes

Reaction equation

HRID 1638370 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]=[C: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 178507081HCID 178507081, compound

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 (0.0935 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 imidazolyl-sodium in 60 ml of n-propanol at the reflux temperature. The reaction mixture is stirred under reflux for a further 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 in diisopropyl ether. The crystalline precipitate formed is filtered off under suction and dried. 12.7 g (35% of theory) of 2,4-bis(4-chlorophenyl)-3,3-dimethyl-1-(imidazol-1-yl)-butan-2-ol of melting point 174° C. are obtained.

Workup

  1. temperatureunder reflux for a further 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 in diisopropyl ether
  7. customThe crystalline precipitate formed
  8. filtrationis filtered off under suction
  9. customdried

Sources & evidence

ORD record
ord-7e1975b52d51478ca1e78c64f0c10fef
Source dataset
uspto-grants-1989_11
Patent number
US04879385

Reaction notes

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