Reaction #89919

Reaction equation

NaOH

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

NaOH

→

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

Yield 94.7%

Solvents

water

EtOH

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Washwashed with CH2Cl2 (2×25 mL)
3. 3
   Extractionextracted with EtOAc (3×50 mL)
4. 4
   DryingThe combined organics were dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo

Procedure

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%).

Source