반응 #54363

반응 방정식

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

반응 조건

후처리

1. 1
   온도The reaction mixture is refluxed for 30 minutes longer
2. 2
   온도the mixture heated
3. 3
   온도to reflux for 1.5 hours
4. 4
   기타The reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   기타the ether layer is separated
6. 6
   추출the aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   건조The combined ether extracts are dried over magnesium sulfate
8. 8
   농축concentrated under vacuum
9. 9
   기타to yield an oil
10. 10
    여과The catalyst is filtered off
11. 11
    기타the ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

실험 절차

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.

출처