Reacción #2735

Ecuación de reacción

ethyl 4-hydroxybenzoate

potassium carbonate

acetone

→

ethyl 4-(2,4-nonadiynyloxy)-benzoate

Rendimiento 70.0%

Disolventes

—

ice water

hexane ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaby heating for 11 hours
2. 2
   Extracciónthe product was extracted with methylene chloride
3. 3
   workup.DISTILLATIONAfter distilling off the solvent of the organic layer
4. 4
   Otrothe residue formed
5. 5
   Otrowas purified by a silica gel column chromatography(developing solvent

Procedimiento

In a flask were placed 3.78 g (0.024 mole) of 1-chloro-2,4-nonadiyne thus obtained, 3.32 g (0.02 mole) of ethyl 4-hydroxybenzoate, 5.5 g (0.04 mole) of potassium carbonate, and 50 ml of acetone and the mixture was refluxed by heating for 11 hours. After allowing to cool the reaction mixture to room temperature, the reaction mixture was poured in 250 ml of ice-water and the product was extracted with methylene chloride. After distilling off the solvent of the organic layer, the residue formed was purified by a silica gel column chromatography(developing solvent: hexane/ethyl acetate=3/1) to provide 4.0 g (yield 70%) of ethyl 4-(2,4-nonadiynyloxy)-benzoate.

Fuente