Phenol → 2-Phenoxymethyl-quinoline

HRID 4372

Reaktionsgleichung

Reaktionsgleichung von HRID 4372
Cl[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CC(C)=O>[O:19]([CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 5

HCID 996PhenolHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinoline

Produkt 1

HCID 137703592-Phenoxymethyl-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloromethyl quinoline (0.05 mol), phenol (0.055 mol), finely powdered potassium carbonate (0.055 mol), cesium carbonate (0.005 mol) and sodium iodide (0.0025 mol) in acetone was refluxed for about 4 hours. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated and dissolved in ether. The ether solution was washed thoroughly with lN NaOH solution, water and brine. After drying the ether solution over anhydrous magnesium sulfate, and filtering off the drying agent, the solvent was evaporated off to leave the crude product which was crystallized from hexane and ether to yield the desired compound as a light yellow solid, m.p. 79.5°-80.5° C.

Aufarbeitung

  1. temperaturewas refluxed for about 4 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated
  4. dissolutiondissolved in ether
  5. washThe ether solution was washed thoroughly with lN NaOH solution, water and brine
  6. dry with materialAfter drying the ether solution over anhydrous magnesium sulfate
  7. filtrationfiltering off the drying agent
  8. customthe solvent was evaporated off
  9. customto leave the crude product which
  10. customwas crystallized from hexane and ether

Quellen und Nachweise

ORD-Eintrag
ord-735fc3dbd8da40b9ad499f1ee9ee5a7e
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725619

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