Hydrogen Peroxide → HCID 66722684, compound

HRID 1639531Notes

Reaction equation

HRID 1639531 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[CH:19]=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.Cl([O-])=[O:24].[Na+]>C(#N)C>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][C:10]=1[C:19]([OH:24])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 21840988HCID 21840988, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 66722684HCID 66722684, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customto remove most of the acetonitrile
  3. extractionThe aqueous acidic solution is extracted with ethyl acetate several times
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-c188f3067f074d8a8e4c31212d69f37e
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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