Acetic Acid → 1-(2-Nitroethenyl)-3-phenoxybenzene

HRID 640247Notes

Reaction equation

HRID 640247 reaction equation
C(O)(=O)C.[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:20]([CH3:23])([O-:22])=[O:21].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[N+:20](/[CH:23]=[CH:15]/[C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:13]=1)([O-:22])=[O:21]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6375NitromethaneHCID 382843-PhenoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 57025051-(2-Nitroethenyl)-3-phenoxybenzeneYield 98.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To an acetic acid (20.0 mL) solution of 3-phenoxybenzaldehyde (3.00 g, 15.1 mmol) were added nitromethane (4.61 g, 75.5 mmol) and ammonium acetate (2.33 g, 30.2 mmol) under nitrogen atmosphere at room temperature, which was stirred for 3 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.60 g) as a crude product.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-ad57c4c8b27f4a8ba2c188495163e723
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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