Réaction #2383786

Équation de réaction

4-chlorobutyric acid

allyl alcohol

hexane

→

title compound

Rendement 79.0%

Allyl 4-chlorobutyrate

Rendement 79.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThe obtained mixture was heated for 5 hours
3. 3
   Autrewas simultaneously removed with Dean-Stark apparatus (Vogel's Textbook of Practical Organic Chemistry, Fourth Ed., Longman, London, 1978, p. 411)
4. 4
   SéchageThe obtained solution was dried with magnesium sulfate
5. 5
   Filtrationafter the filtration of the drying agent hexane
6. 6
   Autrewas evaporated
7. 7
   workup.DISTILLATIONThe crude residue was distilled under reduced pressure 10 mbar at the temperature of 95° C.

Mode opératoire

To a mixture of 4-chlorobutyric acid (48 ml; 0.48 mole), allyl alcohol (200 ml) and hexane (1.2 l) p-toluenesulfonic acid (16.0 g; 0.08 mole) was added. The obtained mixture was heated for 5 hours at reflux temperature in such a way that water was simultaneously removed with Dean-Stark apparatus (Vogel's Textbook of Practical Organic Chemistry, Fourth Ed., Longman, London, 1978, p. 411). The mixture was then cooled to room temperature and shaken with 7% aqueous sodium hydrogencarbonate solution (2×500 ml). The obtained solution was dried with magnesium sulfate and after the filtration of the drying agent hexane was evaporated. The crude residue was distilled under reduced pressure 10 mbar at the temperature of 95° C. and the title compound (61.2 g; 79%) was obtained in the form of a colourless oil.

Source