تفاعل #54363

معادلة التفاعل

ethanol

hydrochloric acid

1-bromopropylbenzene

magnesium

ether

ether

ether

→

title product

2-(3-Methoxyphenyl)-5-phenylpentane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction mixture is refluxed for 30 minutes longer
2. 2
   درجة الحرارةthe mixture heated
3. 3
   درجة الحرارةto reflux for 1.5 hours
4. 4
   أخرىThe reaction is quenched by addition of saturated ammonium chloride (234 ml.)
5. 5
   أخرىthe ether layer is separated
6. 6
   استخلاصthe aqueous phase extracted with ether (3 × 200 ml.)
7. 7
   تجفيفThe combined ether extracts are dried over magnesium sulfate
8. 8
   تركيزconcentrated under vacuum
9. 9
   أخرىto yield an oil
10. 10
    ترشيحThe catalyst is filtered off
11. 11
    أخرىthe ethanol removed under vacuum
12. 12
    workup.DISTILLATIONThe residue is distilled under vacuum

الإجراء التجريبي

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.

المصدر