Nitromethane → 1,2-Dichloro-4-[(E)-2-nitroethenyl]benzene

HRID 1843975Notes

Reaction equation

HRID 1843975 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=O.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>C(O)C>[Cl:10][C:9]1[CH:8]=[CH:7][C:4](/[CH:5]=[CH:14]/[N+:11]([O-:13])=[O:12])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 53722591,2-Dichloro-4-[(E)-2-nitroethenyl]benzeneYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using analogous conditions and workup as described for the preparation of intermediate I-1a above, 3,4-dichlorobenzaldehyde (10 g, 74.074 mmol) in ethanol (100 mL) was reacted with nitro methane (4.12 mL, 74.074 mmol) and 10N NaOH (2.96 g in 7.4 mL of H2O, 74.074 mmol) to afford 6.2 g of the product (39% yield).

Workup

  1. customas described for the preparation of intermediate

Sources & evidence

ORD record
ord-c74a5dc2564f4166bbc319471dbfdaad
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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