ETHYL 3-BUTENOATE

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 4350, 1964 DOI: 10.1021/ja01074a023
The Journal of Organic Chemistry, 49, p. 1341, 1984 DOI: 10.1021/jo00182a005

Synthesis

The synthesis of ETHYL 3-BUTENOATE is as follows:
step one: At room temperature,to a three-necked flask was added 600 parts of toluene,150 parts of triethylamine, 110 parts of ethanol,100 parts of crotonyl chloride were charged in a constant pressure separatory funnel, under electric stirring, toluene.The mixture of triethylamine and ethanol is mixed well, while heating the mixture to 55 °C, then through the constant pressure funnel control crotonyl chloride uniform dropping 1h, reaction overnight, gas chromatography to detect the progress of the reaction, record the reaction time;step two: The reaction is over. The reaction solution is cooled, the liquid is washed twice with water, dried over anhydrous magnesium sulfate, filtering, removing toluene solvent by rotary evaporation, 3-butenoic acid hexyl ester to give a crude product.

step three: The crude 3-butenyl caproate obtained in step two is in a ratio by weight of crude product: silica gel = 3-4: 1 with 120 mesh silica gel dry packing method, then the volume ratio of petroleum ether - ethyl acetate gradient elution, the eluate obtained by eluting with petroleum ether-ethyl acetate in a volume ratio of 200: 1 was recovered, rotary evaporation of petroleum ether - ethyl acetate. The product, hexyl 3-butenoate, weight and calculate yield.