Реакция #89919

Уравнение реакции

NaOH

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

NaOH

→

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

Выход 94.7%

Растворители

water

EtOH

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Промывкаwashed with CH2Cl2 (2×25 mL)
3. 3
   Экстракцияextracted with EtOAc (3×50 mL)
4. 4
   СушкаThe combined organics were dried (Na2SO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo

Методика

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%).

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