Réaction #2735

Équation de réaction

ethyl 4-hydroxybenzoate

potassium carbonate

acetone

→

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

Rendement 70.0%

Solvants

—

ice water

hexane ethyl acetate

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source