Reaction #1726713

Reaction equation

sodium chlorite

methyl 4-benzyloxy-3-formylbenzoate

hydrogen peroxide

→

methyl 4-benzyloxy-3-carboxybenzoate

Yield 100.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Concentrationthe reaction mixture is concentrated
2. 2
   Otherto remove most of the acetonitrile
3. 3
   ExtractionThe aqueous acidic solution is extracted with ethyl acetate several times
4. 4
   WashThe combined extracts are washed with brine
5. 5
   Dryingdried over Na2SO4

Procedure

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.

Source