Reaction #54363

Reaction equation

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is refluxed for 30 minutes longer
2. 2
   Temperaturethe mixture heated
3. 3
   Temperatureto reflux for 1.5 hours
4. 4
   OtherThe reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   Otherthe ether layer is separated
6. 6
   Extractionthe aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   DryingThe combined ether extracts are dried over magnesium sulfate
8. 8
   Concentrationconcentrated under vacuum
9. 9
   Otherto yield an oil
10. 10
    FiltrationThe catalyst is filtered off
11. 11
    Otherthe ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

Procedure

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.

Source