Réaction #46727

Équation de réaction

NH4Cl

1-bromononane

HCl

3-methoxy benzaldehyde

→

pure product

Rendement 64.0%

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

Rendement 64.0%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Températureto maintain slow reflux
2. 2
   workup.ADDITIONafter the end of addition
3. 3
   Températurecooled on an ice/water bath
4. 4
   AutreThe organic phase was isolated
5. 5
   Séchagedried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Autrepurified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:10)

Mode opératoire

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.

Source