Nitroethane → HCID 54306765, compound

HRID 1785429Notes

Reaction equation

HRID 1785429 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=O)[CH:5]=1.C([O-])(=O)C.[NH4+].[N+:18]([CH2:21][CH3:22])([O-:20])=[O:19]>>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[C:21]([N+:18]([O-:20])=[O:19])[CH3:22])[CH:5]=1

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 517165Ammonium AcetateHCID 639145Methyl 3-formylbenzoate

Product 1

HCID 54306765HCID 54306765, compound

Procedure

To a 250 mL round bottom flask was added 3-formyl-benzoic acid methyl ester (2.20 g, 13.4 mmol), ammonium acetate (1.03 g, 13.4 mmol), and nitroethane (60 mL). Mixture heated to reflux under an atmosphere of nitrogen while stirring for 1.5 h. Solvent removed under vacuum then residue partitioned between ethyl acetate (100 mL) and 5% sodium bicarbonate. Organic washed with saturated sodium chloride, dried with magnesium sulfate, then concentrated to a oil under vacuum. Product purified on silica and isolated as a yellow solid. 1H NMR (CDCl3) s (3H, 2.47 ppm), s (3H, 3.96 ppmm), t (1H, 7.55 ppm), d (2H, 7.61 ppm) m (3H, 8.09 ppm).

Workup

  1. temperatureMixture heated
  2. temperatureto reflux under an atmosphere of nitrogen
  3. customSolvent removed under vacuum
  4. customresidue partitioned between ethyl acetate (100 mL) and 5% sodium bicarbonate
  5. washOrganic washed with saturated sodium chloride
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated to a oil under vacuum
  8. customProduct purified on silica
  9. customisolated as a yellow solid

Sources & evidence

ORD record
ord-a820332cb9344d6e98a8146195b03288
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…