Dibromomethane → 1,3-Benzodioxole-4-carboxaldehyde

HRID 1904955Notes

Reaction equation

HRID 1904955 reaction equation
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu]=O>[CH2:12]1[O:10][C:9]2[C:2](=[C:3]([CH:6]=[CH:7][CH:8]=2)[CH:4]=[O:5])[O:1]1

Participants

6

Reactant 3

HCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 905792,3-Dihydroxybenzaldehyde

Product 1

HCID 822641,3-Benzodioxole-4-carboxaldehydeYield 85.6%

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture containing 2,3-dihydroxybenzaldehyde, (50 g) dibromomethane (188 g), potassium carbonate (150 g) and copper (II) oxide (1.4 g) in dimethylformamide (2 L) was heated at reflux for 4 hours. The reaction mixture was cooled, filtered and evaporated. The residue was dissolved in toluene and the organic layer was washed with staurated sodium bicarbonate and brine. The layer was then dried, filtered and evaporated to yield 46.5 g of 2,3-methylenedioxybenzaldehyde mp 32°-33° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was dissolved in toluene
  7. washthe organic layer was washed with staurated sodium bicarbonate and brine
  8. customThe layer was then dried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-b44188de1b5243b1b96fca3b8a582b8e
Source dataset
uspto-grants-1989_06
Patent number
US04840965

Reaction notes

Loading…