4-Chlorophenol → HCID 13176301, compound

HRID 1981303Notes

Reaction equation

HRID 1981303 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:16][C:17](=[O:23])[C:18]([CH3:22])([CH3:21])[CH:19]=[CH2:20]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:16][C:17](=[O:23])[C:18]([CH3:22])([CH3:21])[CH:19]=[CH2:20])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 13102421HCID 13102421, compound

Product 1

HCID 13176301HCID 13176301, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

92.9 g (0.723 mol) of 4-chlorophenol were heated to the boil with 99.7 g (0.723 mol) of finely powdered potassium carbonate in 500 ml of acetone. 106 g (0.723 mol) of 5-chloro-3,3-dimethylpent-1-en-4-one were added dropwise to the mixture in the course of 30 minutes, while stirring vigorously. After the mixture had been heated under reflux for four hours, it was cooled to 20° C. and filtered off from the inorganic salts, and the filtrate was concentrated. After the liquid residue had been distilled, 136.3 g (79% of theory) of 5-(4-chlorophenoxy)-3,3-dimethylpent-1-en-4-one of boiling point 111° to 113° C./0.07 mm Hg were obtained. ##STR28##

Workup

  1. temperatureAfter the mixture had been heated
  2. temperatureunder reflux for four hours
  3. filtrationfiltered off from the inorganic salts
  4. concentrationthe filtrate was concentrated
  5. distillationAfter the liquid residue had been distilled

Sources & evidence

ORD record
ord-c65be6fc3c1f43e69bb9e6d45bf78440
Source dataset
uspto-grants-1985_04
Patent number
US04514409

Reaction notes

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