Nitroethane → HCID 2063266, compound

HRID 1873861Notes

Reaction equation

HRID 1873861 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[N+:11]([CH2:14][CH3:15])([O-:13])=[O:12].C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1/[CH:4]=[C:14](/[N+:11]([O-:13])=[O:12])\[CH3:15]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 134042,4-DichlorobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 2063266HCID 2063266, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

In a sulfonation flask 2,4-dichloro-benzaldehyde (77 g, 0.44 mol), nitroethane (216 ml, 3.04 mol) and ammonium acetate (81.4 g, 1.06 mol) were added to glacial acetic acid (600 ml). The resulting solution was heated to 90° C. for three hours. After removal of the solvent ice-water (400 ml) was added. The solid product was collected by filtration, washed with water and recrystallized from ethanol. 55.9 g (55% of theory) of 2,4-dichloro-1-((E)-2-nitro-propenyl)-benzene was obtained in the form of a yellow solid (m.p. 79-81° C.).

Workup

  1. customAfter removal of the solvent ice-water (400 ml)
  2. additionwas added
  3. filtrationThe solid product was collected by filtration
  4. washwashed with water
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-54c3d0323e564db8b3057d7b3fb7aa5e
Source dataset
uspto-grants-2012_11
Patent number
US08304444B2

Reaction notes

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