4-Chlorophenol → HCID 18919357, compound
Reaction equation
Cl[CH:2]([CH2:6][CH3:7])[C:3](=[O:5])[CH3:4].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.C(=O)(O)[O-].[K+].[I-].[K+]>CC(C)=O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH:2]([CH2:6][CH3:7])[C:3](=[O:5])[CH3:4])=[CH:11][CH:10]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-chloro-2-pentanone (10 g) in acetone (50 ml) was added dropwise to a stirred mixture of 4-chlorophenol (11 g), potassium bicarbonate (20 g) and potassium iodide (1 g) in acetone (100 ml). After the addition was completed the mixture was heated under reflux for 6 hours. The mixture was then filtered, washed with acetone and the acetone was evaporated under reduced pressure. The residue was dissolved in ether (150 ml), and the ethereal mixture was washed with 300 ml of a 10% aqueous solution of sodium hydroxide followed by 300 ml of water. The mixture was then dried over magnesium sulphate. The solvent was evaporated and the residue was distilled under reduced pressure to give 3-(4-chlorophenoxy)-2-pentanone (10.96 g).
Workup
- additionAfter the addition
- temperaturewas heated
- temperatureunder reflux for 6 hours
- filtrationThe mixture was then filtered
- washwashed with acetone
- customthe acetone was evaporated under reduced pressure
- dissolutionThe residue was dissolved in ether (150 ml)
- washthe ethereal mixture was washed with 300 ml of a 10% aqueous solution of sodium hydroxide
- dry with materialThe mixture was then dried over magnesium sulphate
- customThe solvent was evaporated
- distillationthe residue was distilled under reduced pressure
Sources & evidence
- ORD record
- ord-d8eb8299a8eb4ee096bf12b7af8327df
- Source dataset
- uspto-grants-1998_05
- Patent number
- US05753665
Reaction notes
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