Hydrogen Peroxide → 1,3-Dioxaindane-4-carboxylic acid

HRID 2301516Notes

Reaction equation

HRID 2301516 reaction equation
[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[O:2]1.C(=O)([O-])[O-:13].[K+].[K+].OO>CO>[CH2:1]1[O:11][C:10]2[C:3](=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]([OH:13])=[O:6])[O:2]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 822641,3-Benzodioxole-4-carboxaldehyde

Product 1

HCID 3048321,3-Dioxaindane-4-carboxylic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2,3-(methylenedioxy)benzaldehyde (160mg, 1.06mmol), potassium carbonate (960 mg, 6.9 mmol) and 2.4mL of hydrogen peroxide (30-32 wt.% solution in water) in 10 mL of methanol was stirred for 16 hours at room temperature. The mixture was washed with diethyl ether. The water layer was acidified with 1 N aq. HCl to pH>1, then extracted with ethyl acetate. The organic layer was dried over MgSO4, then concentrated to give the desired product (170mg, 96%). EI-MS (m/z) 164.8 (M−).

Workup

  1. washThe mixture was washed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-322973f0b4604d3fb06ecad27fc8b285
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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