1-Naphthaldehyde → 2-Nitro-1-(2-methoxy-1-naphthyl)propene

HRID 1451544Notes

Reaction equation

HRID 1451544 reaction equation
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:13]([O-:16])(=O)C.[NH4+].[N+:18]([CH2:21][CH3:22])([O-:20])=[O:19]>>[N+:18]([C:21]([CH3:22])=[CH:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:16][CH3:13])([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 61951-NaphthaldehydeHCID 6587NitroethaneHCID 517165Ammonium Acetate

Product 1

HCID 542315602-Nitro-1-(2-methoxy-1-naphthyl)propeneYield 95%

Procedure

2.13 g (11.20×10-3 mol) of naphthaldehyde, 30 cm3 of nitroethane and 0.54 g (7×10-3 mol) of ammonium acetate are introduced into a round-bottomed flask. The mixture is stirred and heated to reflux for 2 hours. The nitroethane is then evaporated off under reduced pressure, the residue is taken up with CH2Cl2 and water is added to hydrolyze the acetate. After separation of the two phases, the organic phase is washed with water, the aqueous phases with CH2Cl2 (twice). The organic phase is then dried over MgSO4 and concentrated under reduced pressure. 2.59 g (10.64×10-3 mol) of the expected nitroethylenic compound (yellow solid) are then contained, equivalent to a 95% yield.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customThe nitroethane is then evaporated off under reduced pressure
  4. additionis added
  5. customAfter separation of the two phases
  6. washthe organic phase is washed with water
  7. dry with materialThe organic phase is then dried over MgSO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-260ccd7c489d42e4b0d8a11267147a18
Source dataset
uspto-grants-1997_02
Patent number
US05604261

Reaction notes

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