Reacción #89919

Ecuación de reacción

NaOH

benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate

NaOH

→

5-(benzyloxy)-4-methoxy-2-nitrobenzoic acid

Rendimiento 94.7%

Disolventes

water

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Lavadowashed with CH2Cl2 (2×25 mL)
3. 3
   Extracciónextracted with EtOAc (3×50 mL)
4. 4
   SecadoThe combined organics were dried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated in vacuo

Procedimiento

To a solution of benzyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (1.4 g, 3.56 mmol) in EtOH (10 mL) was added 1N NaOH (4.27 mL, 4.27 mmol). The mixture was stirred at RT for 1 h, upon which an additional aliquot of NaOH (4.27 mL, 4.27 mmol) was added. Stirring was continued at RT overnight. The mixture was diluted with water (20 mL) and washed with CH2Cl2 (2×25 mL). The aqueous layer was acidified to pH=2 with 0.5 N HCl and extracted with EtOAc (3×50 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to give 5-(benzyloxy)-4-methoxy-2-nitrobenzoic acid (1.02 g, 3.37 mmol, 94%).

Fuente