Reacción #46727

Ecuación de reacción

NH4Cl

1-bromononane

HCl

3-methoxy benzaldehyde

→

pure product

Rendimiento 64.0%

1-Methoxy-3-non-1-enyl benzene

Rendimiento 64.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato maintain slow reflux
2. 2
   workup.ADDITIONafter the end of addition
3. 3
   Temperaturacooled on an ice/water bath
4. 4
   OtroThe organic phase was isolated
5. 5
   Secadodried (MgSO4)
6. 6
   Filtraciónfiltered
7. 7
   Otropurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10)

Procedimiento

To dry diethyl ether (50 mL) containing Mg turnings (1.22 g; 50 mmol) under N2 was added 1-bromononane (8.6 mL; 50 mmol) at a rate sufficient to maintain slow reflux. The reaction mixture was stirred for 45 minutes after the end of addition, cooled on an ice/water bath and 3-methoxy benzaldehyde (6.1 mL; 50 mmol) was then added drop wise. The reaction mixture was allowed to warm to room temperature overnight, added saturated aqueous NH4Cl (50 mL) and then 4 M HCl (aq.; 10 mL). The organic phase was isolated, dried (MgSO4), filtered and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10) to yield 7.4 g (64%) pure product.

Fuente