Reacción #46730

Ecuación de reacción

NH4Cl

diethyl ether

1-bromo-2-methoxy-nonyl benzene

HCl

dry Ice

→

pure product

Rendimiento 20.0%

2-Methoxy-4-nonyl benzoic acid

Rendimiento 20.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITION1,2-Dioiodoethane was added
2. 2
   Otrothe reaction
3. 3
   workup.STIRRINGafter additional stirring for 1 hour
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.=1:5)

Procedimiento

To dry diethyl ether (10 mL) containing Mg turnings (0.24 g; 10 mmol) under N2 was added 1-bromo-2-methoxy-nonyl benzene (3.1 g; 10 mmol). 1,2-Dioiodoethane was added to initiate the reaction. Solid dry Ice (excess) was added after stirring for 1 hour and after additional stirring for 1 hour was added sat. NH4Cl (aq.; 20 mL) and then 4 M HCl (aq.; 2 mL). The organic phase was isolated, dried (MgSO4), filtered and purified by column chromatography (SiO2; EtOAc/PE80-100° C.=1:5) to yield 600 mg (20%) pure product.

Fuente