Reaction #1552040

Reaction equation

sebacic acid

hydroquinone

p-toluenesulfonic acid

→

sebacic acid divinyl ester

Solvents

vinyl acetate

ethyl acetate

Conditions

Workup

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

Procedure

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.

Source