4-Chlorophenol → HCID 23465922, compound

HRID 443846Notes

Reaction equation

HRID 443846 reaction equation
[Na].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.Br.Br[CH:12]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH:12]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)[C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 5360545Sodium2×HCID 23465921HCID 23465921, compound

Product 1

HCID 23465922HCID 23465922, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.9 g (0.3 mol) of sodium metal were added to a solution of 38.6 g (0.3 mol) of 4-chlorophenol in 200 ml of absolute methanol. When the sodium had dissolved completely, the solution was heated under reflux and 33.7 g (0.1 mol) of 1-bromo-3,3-dimethyl-1-pyridin-3-yl-butan-2-one hydrobromide were added. The reaction mixture was heated under reflux overnight. It was allowed to cool and was concentrated in vacuo. The residue was taken up in diethyl ether and the ether mixture was washed twice with 2 N sodium hydroxide solution, once with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue was recrystallized from n-hexane. 18.8 g (62% of theory) of 1-(4-chlorophenoxy)-3,3-dimethyl-1-pyridin-3-yl-butan-2-one of melting point 50° C. were obtained.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureto cool
  6. concentrationwas concentrated in vacuo
  7. washthe ether mixture was washed twice with 2 N sodium hydroxide solution, once with water and once with saturated sodium chloride solution
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-0cb2248982ca4c24a1c24cc1df211160
Source dataset
uspto-grants-1981_04
Patent number
US04262000

Reaction notes

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