Nitric Acid → 6-Nitroveratraldehyde

HRID 570019Notes

Reaction equation

HRID 570019 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[N+:13]([O-])([OH:15])=[O:14]>>[CH3:12][O:11][C:10]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([CH:6]=[O:7])=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 8419Veratraldehyde

Product 1

HCID 885056-NitroveratraldehydeYield 61%

Procedure

After reacting 135 g of 3,4-dimethoxybenzaldehyde and 500 ml of conc. nitric acid at 10° C. for 20 hours, the reaction mixture was poured in 3 l of ice water and the resultant crystals were collected by filtration. The crystals were dissolved in a mixed solvent of 8 l of toluene and 500 ml of ethyl acetate. After washing the resultant solution once with a saturated aqueous solution of sodium bicarbonate, three times with water and then once with saturated saline, the solution was concentrated to about 500 ml under reduced pressure. The concentrate was cooled to room temperature and the resultant yellowish crystals (77.71 g) were then collected by filtration (yield: 61%).

Workup

  1. customat 10° C.
  2. customfor 20 hours
  3. filtrationthe resultant crystals were collected by filtration
  4. dissolutionThe crystals were dissolved in a mixed solvent of 8 l of toluene and 500 ml of ethyl acetate
  5. washAfter washing the resultant solution once with a saturated aqueous solution of sodium bicarbonate, three times with water
  6. concentrationonce with saturated saline, the solution was concentrated to about 500 ml under reduced pressure
  7. filtrationthe resultant yellowish crystals (77.71 g) were then collected by filtration (yield: 61%)

Sources & evidence

ORD record
ord-57528dd43db24769ab4f62b4c65602ff
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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