Реакция #1726713

Уравнение реакции

sodium chlorite

methyl 4-benzyloxy-3-formylbenzoate

hydrogen peroxide

→

methyl 4-benzyloxy-3-carboxybenzoate

Выход 100.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Концентрированиеthe reaction mixture is concentrated
2. 2
   Другоеto remove most of the acetonitrile
3. 3
   ЭкстракцияThe aqueous acidic solution is extracted with ethyl acetate several times
4. 4
   ПромывкаThe combined extracts are washed with brine
5. 5
   Сушкаdried over Na2SO4

Методика

To a solution of 1.4 gm (5.2 mmol) of methyl 4-benzyloxy-3-formylbenzoate (prepared by benzylation of methyl 3-formyl-4-hydroxybenzoate) in 25 mL of acetonitrile is added an aqueous solution of NaH2PO4.2H2O (268 mg, 1.68 mmol in 3 mL of water) and 2.8 mL (5 equiv) of 30% hydrogen peroxide. To this mixture is added dropwise an aqueous solution of 79% sodium chlorite (830 mg, 7.25 mmol of NaClO2 in 7 mL of water). After 2 hr at room temperature at room temperature, the reaction mixture is concentrated to remove most of the acetonitrile. The residue is taken up in water and acidified with aqueous HCl. The aqueous acidic solution is extracted with ethyl acetate several times. The combined extracts are washed with brine and dried over Na2SO4. Rotoevaporation of solvent gives 1.5 gm (5.2 mmol) of methyl 4-benzyloxy-3-carboxybenzoate.

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