Nitromethane → 1-((E)-2-Nitro-vinyl)-4-phenoxymethyl-benzene

HRID 1691157Notes

Reaction equation

HRID 1691157 reaction equation
[O:1]([CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[N+:17](/[CH:20]=[CH:13]/[C:12]1[CH:15]=[CH:16][C:9]([CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 121062874-(Phenoxymethyl)benzaldehyde

Product 1

HCID 592552121-((E)-2-Nitro-vinyl)-4-phenoxymethyl-benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-phenoxymethyl-benzaldehyde described in Manufacturing Example 86-1-2 (3.8 g, 17.8 mmol), nitromethane (4.79 mL, 89 mmol), ammonium acetate (2.74 g, 35.6 mmol) and acetic acid (38 mL) was stirred for 3 hours at 100° C. This mixture was cooled to room temperature, concentrated under a reduced pressure, and diluted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (4.1 g).

Workup

  1. temperatureThis mixture was cooled to room temperature
  2. concentrationconcentrated under a reduced pressure
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-25203dfaaf9345998567c5ae7792e99c
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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