Nitroethane → 1-methoxy-3-(2-nitroprop-1-enyl)benzene

HRID 1252190Notes

Reaction equation

HRID 1252190 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:1]=[C:14]([N+:11]([O-:13])=[O:12])[CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 115693-MethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 6062591-methoxy-3-(2-nitroprop-1-enyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 71.9 g (0.528 mole) of m-anisaldehyde, 118.9 g (1.584 mole) of nitroethane, 40.7 g (0.528 mole) of ammonium acetate, and 350 ml of glacial acetic acid was heated to reflux for one hour. The mixture was then allowed to cool and partitioned between ether and water. The ether layer was separated and washed sequentially with water, 3N sodium hydroxide, water and brine. The organic phase was dried over anhydrous magnesium sulfate and evaporated in vacuo to give the crude product. After a preliminary distillation at 125° C./0.0001 mm, the product was finally crystallized from absolute ethanol to yield the pure product, a yellow solid, mp 40°-42° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour
  3. temperatureto cool
  4. custompartitioned between ether and water
  5. customThe ether layer was separated
  6. washwashed sequentially with water, 3N sodium hydroxide, water and brine
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-98a9e04f4d314c5187f922e05b0d6c1e
Source dataset
uspto-grants-1988_05
Patent number
US04742084

Reaction notes

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