Reaktion #89919

Reaktionsgleichung

NaOH

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

NaOH

→

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

Ausbeute 94.7%

Lösungsmittel

water

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Waschenwashed with CH2Cl2 (2×25 mL)
3. 3
   Extraktionextracted with EtOAc (3×50 mL)
4. 4
   TrocknenThe combined organics were dried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo

Vorschrift

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%).

Quelle