Catechol → HCID 20512797, compound

HRID 1164249Notes

Reaction equation

HRID 1164249 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[CH3:9][NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CC(C)=O.[Ag]=O>[CH3:9][N:10]([C:6]1[CH:7]=[CH:8][C:1](=[O:2])[C:3](=[O:4])[CH:5]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 289CatecholHCID 7515N-MethylanilineHCID 24436Sodium Sulfate

Product 1

HCID 20512797HCID 20512797, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Procedure

2.2 g (0.02 mole) catechol and 2.0 g (0.019 mole) N-methylaniline were dissolved in 80 ml acetone. Then 18.8 g (0.08 mole) silver oxide was added followed by 20 g anhydrous sodium sulfate. The mixture was stirred at room temperature for 10 minutes and filtered. The residue was washed with several portions of acetone totaling 50 ml. The filtrate was diluted with ligroin (bp 60°-80° C.) and the solid was filtered and washed with ligroin to give 2.6 g (60%). Thin-layer chromatography on Eastman chromogram silica gel sheets showed essentially a single spot with traces of impurities.

Workup

  1. filtrationfiltered
  2. washThe residue was washed with several portions of acetone totaling 50 ml
  3. additionThe filtrate was diluted with ligroin (bp 60°-80° C.)
  4. filtrationthe solid was filtered
  5. washwashed with ligroin
  6. customto give 2.6 g (60%)

Sources & evidence

ORD record
ord-e3fc38a7e3554b64be33ea236847fe19
Source dataset
uspto-grants-1983_01
Patent number
US04368249

Reaction notes

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