反応 #89919

反応方程式

NaOH

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

NaOH

→

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

収率 94.7%

溶媒

water

EtOH

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   洗浄washed with CH2Cl2 (2×25 mL)
3. 3
   抽出extracted with EtOAc (3×50 mL)
4. 4
   乾燥The combined organics were dried (Na2SO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo

実験手順

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%).

出典