Nitroethane → 1-Chloro-4-(2-nitro-1-propen-1-yl)benzene

HRID 1363478Notes

Reaction equation

HRID 1363478 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].[N+:15]([CH2:18][CH3:19])([O-:17])=[O:16]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:18]([N+:15]([O-:17])=[O:16])[CH3:19])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 77264-ChlorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 1203411-Chloro-4-(2-nitro-1-propen-1-yl)benzeneYield 40%

Conditions

Temperature
105 °C

Procedure

2.00 g (14.2 mmol) 4-chlorobenzaldehyde (Aldrich, Milwaukee, Wis.), 5.48 g (71.1 mmol) ammonium acetate (Fluka), and 50 g (666 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 dark yellow liquid which was recrystallized from cold methyl alcohol three times to give yellow needles in 40% yield. 1H NMR spectra is shown in FIG. 2.

Workup

  1. customequipped with magnetic stirrer and nitrogen inlet
  2. customthe solvent was removed under vacuum
  3. customto give a dark yellow liquid which
  4. customwas recrystallized from cold methyl alcohol three times
  5. customto give yellow needles in 40% yield

Sources & evidence

ORD record
ord-9607113a5dd94b0e9fd639a1d5a9c01e
Source dataset
uspto-grants-2011_02
Patent number
US07884228B1

Reaction notes

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