Acetyl chloride → HCID 21320009, compound

HRID 262154Notes

Reaction equation

HRID 262154 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[N:5]1([CH:10]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:11]([OH:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH:9]=[CH:8][N:7]=[CH:6]1>C(OCC)(=O)C>[C:1]([O:16][CH:11]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:10]([O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 12766922HCID 12766922, compound

Product 1

HCID 21320009HCID 21320009, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.0 g (0.1 mol) of acetyl chloride are added to 20.6 g (0.1 mol) of 1-imidazol-1-yl-1-phenoxy-3,3-dimethyl-butan-2-ol in 100 ml of ethyl acetate at room temperature. The mixture is then heated under reflux for 4 hours. It is allowed to cool and concentrated by distilling off the solvent in vacuo. The residue is taken up in benzene and the solution is washed with aqueous sodium bicarbonate solution and dried over sodium sulphate. The solvent is distilled off under a water pump vacuum and the residue is recrystallized from petroleum ether. 20.6 g (45% of theory) of 2-acetoxy-1-phenoxy-1-imidazol-1-yl-3,3-dimethyl-butane are obtained as a mixture of isomers with a melting point of 114°-121° C.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. concentrationconcentrated
  5. distillationby distilling off the solvent in vacuo
  6. washthe solution is washed with aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulphate
  8. distillationThe solvent is distilled off under a water pump vacuum
  9. customthe residue is recrystallized from petroleum ether

Sources & evidence

ORD record
ord-357cf40c989b44bb97d86753ec770f6c
Source dataset
uspto-grants-1979_05
Patent number
US04153708

Reaction notes

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