反応 #2735

反応方程式

ethyl 4-hydroxybenzoate

potassium carbonate

acetone

→

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

収率 70.0%

溶媒

—

ice water

hexane ethyl acetate

反応条件

後処理

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

実験手順

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.

出典