Reacción #574258

Ecuación de reacción

4,6-diacetylresorcinol

potassium carbonate

5-bromopentanenitrile

potassium iodide

→

desired title product

Rendimiento 24.2%

5-(2,4-Diacetyl-5-hydroxyphenoxy)pentanenitrile

Rendimiento 24.2%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux overnight
3. 3
   ConcentraciónThe mixture was concentrated in vacuo
4. 4
   Otropartitioned between ethyl acetate and dilute hydrochloric acid
5. 5
   OtroThe organic layer was separated
6. 6
   Secadodried over sodium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane

Procedimiento

A mixture of 582 mg of 4,6-diacetylresorcinol, 460 mg of potassium carbonate, 530 mg of 5-bromopentanenitrile and 0.2 9 of potassium iodide was heated at reflux overnight. The mixture was concentrated in vacuo and partitioned between ethyl acetate and dilute hydrochloric acid. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative thin layer chromatography on silica gel eluting with 40% ethyl acetate in hexane to provide 200 mg of the desired title product, m.p.=105°-106° C.

Fuente