Реакция #2067191

Уравнение реакции

n-propylmagnesium bromide

7-methoxy-3,7-dimethyl-1-octene

→

2,6-dimethyl-2-methoxy-9-isopropylphenylnonane

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ДругоеAfter the vigorous reaction
2. 2
   Температураthe mixture was heated in an oil bath (75°) for 19 hours
3. 3
   ДругоеAliquot quench at this point
4. 4
   ДругоеThe Grignard exchange product was transferred to a separatory funnel
5. 5
   workup.ADDITIONadded dropwise to p-isopropylbenzyl chloride (21 g) in THF (300 ml)
6. 6
   workup.ADDITIONcontaining cuprous chloride (2.5 g)
7. 7
   Температураcooled at 0° to -10°
8. 8
   Другоеthe reaction was then quenched with aqueous ammonium chloride
9. 9
   Экстракцияextracted with pentane
10. 10
    workup.DISTILLATIONThe pentane extracts were distilled

Методика

To a solution of n-propylmagnesium bromide (0.25 mole) in tetrahydrofuran (200 ml) was added 7-methoxy-3,7-dimethyl-1-octene (42.5 g) and biscyclopentadienyl titanium dichloride (1.25 g). After the vigorous reaction subsided, the mixture was heated in an oil bath (75°) for 19 hours. Aliquot quench at this point indicated ~50% conversion. The Grignard exchange product was transferred to a separatory funnel, and added dropwise to p-isopropylbenzyl chloride (21 g) in THF (300 ml) containing cuprous chloride (2.5 g) cooled at 0° to -10° while stirring. On warming to room temperature overnight, the reaction was then quenched with aqueous ammonium chloride and extracted with pentane. The pentane extracts were distilled to give product (2,6-dimethyl-2-methoxy-9-isopropylphenylnonane) (12.5 g; bp 150°-152° /0.25-0.3 torr) contaminated with some p, p'-diisopropylbibenzyl.

Источник