1,2-Dibromoethane → 2,3-Dihydro-1,4-benzodioxin-6-carbaldehyde

HRID 1980794Notes

Reaction equation

HRID 1980794 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH2:11](Br)[CH2:12]Br.[OH-].[Na+]>[Cu].C(O)C>[CH2:11]1[CH2:12][O:10][C:9]2[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=2[O:1]1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 87683,4-DihydroxybenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehyde

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Procedure

(i)(a) A mixture of 3,4-dihydroxybenzaldehyde (10.0 g), ethylene dibromide (13.61 g), copper powder (trace), sodium hydroxide (5.80 g) and ethanol (500 ml) was heated at reflux for 2 days. Subsequently, the solvent was evaporated and the residue was dissolved in dichloromethane. The organic phase was shaken with a little water and then dried over anhydrous magnesium sulphate. The solvent was evaporated and the residue was purified by column chromatography over silica gel (eluant dichloromethane) giving 3,4-ethylenedioxybenzaldehyde as an oil. The product was characterized by proton nuclear magnetic resonance spectroscopy. Pmr spectrum (CDCl3 ; δ in ppm): 4.35 (4H, s); 6.98 (1H, d); 7.40 (2H, m); 9.70 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customSubsequently, the solvent was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was evaporated
  7. customthe residue was purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-2305406800a746c5aa81ef40ebeca390
Source dataset
uspto-grants-1985_04
Patent number
US04511391

Reaction notes

Loading…