Ethanol → Benzene, 1,3-dichloro-5-nitro-

HRID 426923

Reaction equation

HRID 426923 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[C:3]=1N.C(O)C.[N+]([O-])([O-])=O.[Na+].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[C:5]([Cl:12])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 74302,6-Dichloro-4-nitroanilineHCID 24268Sodium Nitrate

Product 1

HCID 12064Benzene, 1,3-dichloro-5-nitro-Yield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An article in Journal of the American Chemical Society, 72 (1950), 798, discloses that 2,6-dichloro-4-nitroaniline, ethanol and sodium nitrate can be reacted at the boil, in the absence of water and in the presence of concentrated sulfuric acid, to give an 84% yield of 3,5-dichloronitrobenzene. A corresponding reaction to form the 3,5-dibromonitrobenzene proceeds with a yield of 91%. The process is unsatisfactory in respect of the yield and purity of the end product and in respect of simple, reliable and economical operation, particularly on an industrial scale.

Sources & evidence

ORD record
ord-65ff04a079b54b56a28b1ea15f90fd05
Source dataset
uspto-grants-1979_10
Patent number
US04172098

Linked notes

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