Carbon Dioxide → 5-(3,4-Dimethoxyphenyl)furan-2-carbaldehyde

HRID 1759146Notes

Reaction equation

HRID 1759146 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])N.C(=O)=O.N([O-])=O.[Na+].[O:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[CH:26]=[O:27]>O.CC(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:25]2[O:21][C:22]([CH:26]=[O:27])=[CH:23][CH:24]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 7362FurfuralHCID 1182453,4-Dimethoxyanilinium chlorideHCID 23668193Sodium Nitrite

Product 1

HCID 123749575-(3,4-Dimethoxyphenyl)furan-2-carbaldehydeYield 27%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent3×

Procedure

A 12 l. four-necked flask equipped with a stirrer, a thermometer and a dropping funnel was charged with water (5 l.). Hydrochloric acid (500 ml) was introduced dropwise. 3,4-dimethoxyaniline hydrochloride (379 g, 2.0 moles) was introduced. This mixture was cooled to -5° C. with a mixture of dry ice and acetone. A solution of sodium nitrite (200 g, 2.9 moles) in water (1600 ml) was introduced dropwise maintaining the temperature at -5° to 0° C. This was followed by the addition of furaldehyde (384 g, 4.0 moles) at -5° C. as fast as possible. A solution of CuCl2.2H2O (112 g) in water (500 ml) was introduced. Stirring was continued for 8 days at ambient temperature. The contents of the flask was extracted with ether (3×3 l.). The combined extracts were dried over MgSO4 overnight. The mixture was filtered and the drying agent was washed with anhydrous ether. The solvent was removed in vacuo. The excess furfural was removed by using an oil pump and a water bath having a maximum temperature of 63° C. The residue was triturated with a minimum amount of isopropanol and ice cooled. The semi-solid was filtered off and washed with isopropanol. The obtained solid was stirred with fresh isopropanol (500 ml) and filtered to give 125 g of the product (27%).

Workup

  1. customfour-necked flask equipped with a stirrer
  2. temperaturemaintaining the temperature at -5° to 0° C
  3. extractionThe contents of the flask was extracted with ether (3×3 l.)
  4. dry with materialThe combined extracts were dried over MgSO4 overnight
  5. filtrationThe mixture was filtered
  6. washthe drying agent was washed with anhydrous ether
  7. customThe solvent was removed in vacuo
  8. customThe excess furfural was removed
  9. customa maximum temperature of 63° C
  10. customThe residue was triturated with a minimum amount of isopropanol and ice
  11. temperaturecooled
  12. filtrationThe semi-solid was filtered off
  13. washwashed with isopropanol
  14. stirringThe obtained solid was stirred with fresh isopropanol (500 ml)
  15. filtrationfiltered

Sources & evidence

ORD record
ord-c9f9073d3e4f41bca0973d985d35124b
Source dataset
uspto-grants-1982_07
Patent number
US04339386

Reaction notes

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