Nitroethane → HCID 620059, compound

HRID 551767Notes

Reaction equation

HRID 551767 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=O.C([O-])(=O)C.[NH4+].[N+:20]([CH2:23][CH3:24])([O-:22])=[O:21]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:23]([N+:20]([O-:22])=[O:21])[CH3:24])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 68583,4,5-TrimethoxybenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 620059HCID 620059, compoundYield 50%

Conditions

Temperature
105 °C

Procedure

5.00 g (25.5 mmol) 3,4,5-trimethoxybenzaldehyde (Aldrich, Milwaukee, Wis.), 9.82 g (127 mmol) ammonium acetate (Fluka), and 50 g (670 Mmol) nitroethane, 98% (Aldrich) were combined in a 100 ml round bottom flask equipped with magnetic stirrer and nitrogen inlet. The reaction mixture was heated to 105° C. for 90 minutes and the solvent was removed under vacuum to give a crude product which was recrystallized from cold methyl alcohol three times to give yellow needles in 50% yield. 1H NMR spectra is shown in FIG. 4.

Workup

  1. customequipped with magnetic stirrer and nitrogen inlet
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-55b12baff1a4450186eb021a63873531
Source dataset
uspto-grants-2011_05
Patent number
US07947849B2

Reaction notes

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