Toluene → Methyl 4-(4-phenoxyphenoxy)benzoate

Methyl 4-(4-phenoxyphenoxy)benzoate is synthesized as follows. A mixture of 15.00 g (80.6 mmol) of 4-phenoxyphenol, 130 ml of N,N-dimethylformamide and 75 ml of toluene is agitated under nitrogen atmosphere. 9.32 g (80.6 mmol) of potassium t-butoxide is added with vigorous stirring and the mixture is heated to reflux. An azeotrope of t-butanol and toluene (85 ml) is collected at temperatures of 120° C. to 135° C. and is discarded. The mixture is cooled to ambient temperature, and a solution of 14.59 g (80.6 mmol) of methyl 4-nitrobenzoate in 30 ml of N,N-dimethylformamide is added over a period of 15 minutes with cooling in a water bath. The mixture is heated at 100° C. for 14 hours, cooled to 20° C., and quenched with 1500 ml of ice water. The precipitate is filtered, dried in air and dissolved in 500 ml of acetone. The solution is filtered to remove insolubles, and the filtrate is concentrated by evaporation and cooled to precipitate methyl 4-(4-phenoxyphenoxy)benzoate. The recovered product weighs 21.23 g (82 percent yield) and has a melting point of 114° C. as determined by DSC.

1. stirringwith vigorous stirring
2. temperaturethe mixture is heated to reflux
3. customAn azeotrope of t-butanol and toluene (85 ml) is collected at temperatures of 120° C. to 135° C.
4. temperaturewith cooling in a water bath
5. temperatureThe mixture is heated at 100° C. for 14 hours
6. temperaturecooled to 20° C.
7. customquenched with 1500 ml of ice water
8. filtrationThe precipitate is filtered
9. customdried in air
10. dissolutiondissolved in 500 ml of acetone
11. filtrationThe solution is filtered
12. customto remove insolubles
13. concentrationthe filtrate is concentrated by evaporation
14. temperaturecooled
15. customto precipitate methyl 4-(4-phenoxyphenoxy)benzoate

ORD-Eintrag

ord-89498967c13c4a02b2285e972262ea6e

Quelldatensatz

uspto-grants-1991_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05030706