Nitroethane → HCID 73979924, compound

HRID 985585Notes

Reaction equation

HRID 985585 reaction equation
[CH3:1][O:2][C:3]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:4]=1[CH:5]=O.C([O-])(=O)C.[NH4+].[N+:20]([CH2:23][CH3:24])([O-:22])=[O:21]>C(OC(C)C)(C)C>[CH3:13][O:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:3]([O:2][CH3:1])=[C:4]([CH:5]=[C:23]([N+:20]([O-:22])=[O:21])[CH3:24])[C:7]=1[CH3:14]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 136083472,5-Dimethoxy-3,6-dimethylbenzaldehyde

Product 1

HCID 73979924HCID 73979924, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of 2,5-dimethoxy-3,6-dimethyl-benzaldehyde (4.0 g, 20 mmol), ammonium acetate (1 g, 13 mmol) and nitroethane (25 ml) was heated under reflux for 4 hours. The reaction mixture was diluted with diisopropyl ether, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:isopropyl ether=95:5) and then recrystallized from methanol to obtain 5.1 g of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. washwashed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (hexane:isopropyl ether=95:5)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-11b088912a2d4f12909aef8b10cc2960
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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