Reacción #542706

Ecuación de reacción

Catechol

potassium carbonate

2-Chloromethyl-3-chloro-1-propene

→

3-methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepine

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturato reflux for one hour
3. 3
   Temperaturaat reflux for 24 hours
4. 4
   Filtraciónfiltered
5. 5
   OtroThe filtrate was evaporated
6. 6
   workup.ADDITIONthe residue was diluted with water
7. 7
   Extracciónextracted with diethyl ether (3×)
8. 8
   SecadoThe combined organic solution was dried over MgSO4
9. 9
   Concentraciónconcentrated

Procedimiento

Catechol (5.09 g, 46.2 mmol) and potassium carbonate were combined in acetonitrile and heated to reflux for one hour. 2-Chloromethyl-3-chloro-1-propene (5.78 g, 46.2 mmol) was added and the reaction was continued at reflux for 24 hours. The solution was cooled to room temperature and filtered. The filtrate was evaporated and the residue was diluted with water and extracted with diethyl ether (3×). The combined organic solution was dried over MgSO4 and concentrated. Chromatography (2% ethyl ether in hexane) yielded 3-methylene-3,4-dihydro-2H-benzo[b][1,4]dioxepine as a colorless oil.

Fuente