Reaktion #433210

Reaktionsgleichung

phenol

cesium carbonate

2-bromo-3,4-dihydro-7-methoxy-1(2H)-naphthalenone

→

present title product

Ausbeute 61.0%

3,4-Dihydro-7-methoxy-2-phenoxy-1(2H)-naphthalenone

Ausbeute 61.0%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 40 minutes
3. 3
   SonstigeThe resultant reaction mixture
4. 4
   Filtrationfiltrated
5. 5
   SonstigeThe filtrate was evaporated to an oil which
6. 6
   Sonstigewas purified via column chromatography on 400 g of silica gel
7. 7
   Wascheneluting with 25% ether-hexane

Vorschrift

A mixture of 2.95 g (31.4 mmol) of phenol, 25.5 g (78.2 mmol) of cesium carbonate and 320 mg (1.23 mmol) of cesium iodide in 64 ml of acetone was heated at reflux for 40 minutes and then cooled to 0° C. To this 0° C. mixture was added 8.00 g (31.4 mmol) of 2-bromo-3,4-dihydro-7-methoxy-1(2H)-naphthalenone. The resultant reaction mixture was stirred 3 hours at 0° C. and 15 hours at 25° C., then filtrated. The filtrate was evaporated to an oil which was purified via column chromatography on 400 g of silica gel, eluting with 25% ether-hexane, to give 5.14 g (61%) of present title product as an oil, crystallized from ether-hexane, m.p. 94.5°-96.5° C.

Quelle