Reacción #4468

Ecuación de reacción

2-chloromethyl quinoline

phenol

potassium carbonate

cesium carbonate

sodium iodide

→

desired compound

2-Phenoxymethyl quinoline

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for about 4 hours
2. 2
   Filtraciónfiltered
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   workup.DISSOLUTIONdissolved in ether
5. 5
   LavadoThe ether solution was washed thoroughly with lN NaOH solution, water and brine
6. 6
   SecadoAfter drying the ether solution over anhydrous magnesium sulfate
7. 7
   Filtraciónfiltering off the drying agent
8. 8
   Otrothe solvent was evaporated off
9. 9
   Otroto leave the crude product which
10. 10
    Otrowas crystallized from hexane and ether

Procedimiento

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.

Fuente