3,5-Dimethoxyphenol → HCID 18379978, compound

HRID 2299181Notes

Reaction equation

HRID 2299181 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:23])[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].[Cu]I.CN1CCCC1=O>[CH3:22][O:21][C:19]1[CH:18]=[C:17]([CH:16]=[C:15]([O:14][CH3:13])[CH:20]=1)[O:23][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

7

Reactant 3

HCID 103833,5-DimethoxyphenolHCID 11430Potassium CarbonateHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 18379978HCID 18379978, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-5-nitrobenzaldehyde (5.57 g), 3,5-dimethoxyphenol (4.62 g), potassium carbonate (8.29 g), copper powder (0.2 g), copper (I) iodide (0.6 g) and N-methyl-2-pyrrolidone (60 ml) were mixed together and then stirred under heating at 120° C. for 30 minutes. After cooling the reaction mixture to room temperature, the reaction mixture was filtered. The filtrate was diluted with water and extracted with ethyl acetate. The exacted solution was sequentially washed in water and then an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The residue after filtration and concentration was purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=8:2 to 6:4), to recover 2-(3,5-dimethoxyphenoxy)-5-nitrobenzaldehyde (6.54 g; yield of 72%).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was diluted with water
  4. extractionextracted with ethyl acetate
  5. washThe exacted solution was sequentially washed in water
  6. dry with materialan aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  7. filtrationThe residue after filtration and concentration
  8. customwas purified by silica gel column chromatography (elution solvent; hexane:ethyl acetate=8:2 to 6:4)

Sources & evidence

ORD record
ord-9f1b607ea3724a4a9693d200ebcbf8e6
Source dataset
uspto-grants-2002_12
Patent number
US06495592B1

Reaction notes

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