Реакция #54363

Уравнение реакции

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture is refluxed for 30 minutes longer
2. 2
   Температураthe mixture heated
3. 3
   Температураto reflux for 1.5 hours
4. 4
   ДругоеThe reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   Другоеthe ether layer is separated
6. 6
   Экстракцияthe aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   СушкаThe combined ether extracts are dried over magnesium sulfate
8. 8
   Концентрированиеconcentrated under vacuum
9. 9
   Другоеto yield an oil
10. 10
    ФильтрацияThe catalyst is filtered off
11. 11
    Другоеthe ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

Методика

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.

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