Reaktion #54363

Reaktionsgleichung

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture is refluxed for 30 minutes longer
2. 2
   Temperaturthe mixture heated
3. 3
   Temperaturto reflux for 1.5 hours
4. 4
   SonstigeThe reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   Sonstigethe ether layer is separated
6. 6
   Extraktionthe aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   TrocknenThe combined ether extracts are dried over magnesium sulfate
8. 8
   Einengenconcentrated under vacuum
9. 9
   Sonstigeto yield an oil
10. 10
    FiltrationThe catalyst is filtered off
11. 11
    Sonstigethe ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

Vorschrift

A solution of 1-bromopropylbenzene (51.7 g.) in ether (234 ml.) is added dropwise over a 2-hour period to a refluxing mixture of magnesium (7.32 g.) in ether (78 ml.). The reaction mixture is refluxed for 30 minutes longer and then a solution of 3-methoxy-acetophenone (41.6 g.) in ether (78 ml.) is added dropwise and the mixture heated to reflux for 1.5 hours. The reaction is quenched by addition of saturated ammonium chloride (234 ml.), the ether layer is separated and the aqueous phase extracted with ether (3 × 200 ml.). The combined ether extracts are dried over magnesium sulfate and concentrated under vacuum to yield an oil. The oil is hydrogenated in a mixture containing ethanol (300 ml.), concentrated hydrochloric acid (2 ml.) and 5% palladium-on-carbon (5 g.). The catalyst is filtered off and the ethanol removed under vacuum. The residue is distilled under vacuum to give the title product.

Quelle