Methanol → HCID 19829944, compound

HRID 2175376Notes

Reaction equation

HRID 2175376 reaction equation
CO.O.[CH3:4][O:5][C:6]1[CH:22]=[CH:21][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)=[CH:8][CH:7]=1>CO.O.[Fe]>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[NH2:18])=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 36283881-[(4-Methoxyphenyl)Methoxy]-3-nitro-Benzene

Product 1

HCID 19829944HCID 19829944, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

Fe (5.6 g, 100.28 mmol) was mixed with methanol:H2O (15 ml:3 ml) and refluxed for 30 minutes. After the temperature is dropped to room temperature, 1-(4-methoxybenzyloxy)-3-nitrobenzene (1.3 g, 5.01 mmol) dissolved in 6 ml of methanol:H2O (5:1) was added and then refluxed for 15 hours. Fe was removed using cellite, then the reaction mixture was washed using methanol and concentrated under vacuum to remove the solvent. After extraction with 100 ml of saturated ammonium chloride+150 ml of dichloromethane, the organic layer was washed with water. The organic solvent was concentrated under vacuum to obtain the title compound (1.14 g, 99%).

Workup

  1. additionAfter the temperature is dropped to room temperature
  2. additionwas added
  3. temperaturerefluxed for 15 hours
  4. customFe was removed
  5. washthe reaction mixture was washed
  6. concentrationconcentrated under vacuum
  7. customto remove the solvent
  8. extractionAfter extraction with 100 ml of saturated ammonium chloride+150 ml of dichloromethane
  9. washthe organic layer was washed with water
  10. concentrationThe organic solvent was concentrated under vacuum

Sources & evidence

ORD record
ord-04c51b389c0e4850b765aa9505c3d79a
Source dataset
uspto-grants-2015_06
Patent number
US09062066B2

Reaction notes

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