反応 #54363

反応方程式

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

反応条件

後処理

1. 1
   温度The reaction mixture is refluxed for 30 minutes longer
2. 2
   温度the mixture heated
3. 3
   温度to reflux for 1.5 hours
4. 4
   その他The reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   その他the ether layer is separated
6. 6
   抽出the aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   乾燥The combined ether extracts are dried over magnesium sulfate
8. 8
   濃縮concentrated under vacuum
9. 9
   その他to yield an oil
10. 10
    ろ過The catalyst is filtered off
11. 11
    その他the ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

実験手順

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.

出典