Reaktion #1106676

Reaktionsgleichung

Catechol

potassium carbonate

2-Chloromethyl-3-chloro-1-propene

→

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

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for one hour
3. 3
   Temperaturat reflux for 24 hours
4. 4
   Filtrationfiltered
5. 5
   SonstigeThe filtrate was evaporated
6. 6
   workup.ADDITIONthe residue was diluted with water
7. 7
   Extraktionextracted with diethyl ether (3×)
8. 8
   TrocknenThe combined organic solution was dried over MgSO4
9. 9
   Einengenconcentrated

Vorschrift

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.

Quelle