Hydrochloric Acid → HCID 54279517, compound

HRID 849368Notes

Reaction equation

HRID 849368 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[C:17]([N+]([O-])=O)[CH3:18])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl.[OH2:23]>[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:16][C:17](=[O:23])[CH3:18])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 54092347HCID 54092347, compound

Product 1

HCID 54279517HCID 54279517, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

953 mg of 1-(3-methoxy-4-phenoxyphenyl)-2-nitropropene, 1.31 g of iron, 9.5 mg of ferric chloride and 5 ml of water were mixed, and 1.5 ml of 6N hydrochloric acid was dropwise added over a period of 1.5 hours under reflux and heating. The reaction solution was subjected to celite filtration, and the filtrate was extracted with ethyl acetate. The extract solution was washed with a saturated sodium hydrogen carbonate aqueous solution and then, dried over anhydrous sodium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain 688 mg (yield: 80%) of the above identified compound as a colorless oily substance.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. filtrationThe reaction solution was subjected to celite filtration
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract solution was washed with a saturated sodium hydrogen carbonate aqueous solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)
  10. customto obtain 688 mg (yield: 80%) of the

Sources & evidence

ORD record
ord-ace9237d371d4a9694b52a17c9beb594
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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