Реакция #1552040

Уравнение реакции

sebacic acid

hydroquinone

p-toluenesulfonic acid

→

sebacic acid divinyl ester

Растворители

vinyl acetate

ethyl acetate

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was refluxed for 4 hours
2. 2
   Экстракцияextracted with 150 ml 2N NaOH
3. 3
   СушкаThe organic phase was dried over Na2SO4
4. 4
   Другоеthe volatile components were removed on a rotary evaporator
5. 5
   ДругоеPurification by flash column chromatography on silica gel (PE:EE=10:1)
6. 6
   Другоеyielded 8.9 g (47% of th.) of a colorless liquid

Методика

15 g (74.2 mmol) of sebacic acid, 0.66 g (2.06 mmol) of mercury(II)acetate, and 0.12 g of hydroquinone were precharged in 75 ml of vinyl acetate into a 250 ml three-necked flask and stirred for 20 minutes under argon. Then, 0.09 g (0.01 mol) of p-toluenesulfonic acid were added as a catalyst, and the reaction mixture was refluxed for 4 hours. After cooling down to room temperature, the obtained solution was diluted with 200 ml ethyl acetate and extracted with 150 ml 2N NaOH. The organic phase was dried over Na2SO4, and the volatile components were removed on a rotary evaporator. Purification by flash column chromatography on silica gel (PE:EE=10:1) yielded 8.9 g (47% of th.) of a colorless liquid.

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