Hydrochloric Acid → 3,5-Dinitrobenzoyl chloride

HRID 2120315Notes

Reaction equation

HRID 2120315 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].S(Cl)([Cl:18])=O.[N+](C1C([N+]([O-])=O)=C(C=CC=1)C(O)=O)([O-])=O.Cl>CN(C=O)C.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7]([Cl:18])=[O:8])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74333,5-Dinitrobenzoic acidHCID 24386Thionyl ChlorideHCID 2833272,3-Dinitrobenzoic acid

Product 1

HCID 74323,5-Dinitrobenzoyl chlorideYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,5 dinitrobenzoic acid and ethyl acetate were placed in a reaction vessel. While thionyl chloride with some drops of DMF (about double as many moles as dinitrobenzoic acid) was dropped into the reaction mixtures, the reaction mixtures were refluxed with stirring until the generation of hydrogen chloride gas stopped. The reacted solution was concentrated until a solid could be precipitated and was poured into hexane and then the precipitated solid was separated by filtration. 3,5-dinitrobenzoic chloride was obtained in a 90% yield.

Workup

  1. customthe reaction mixtures
  2. temperaturewere refluxed
  3. concentrationThe reacted solution was concentrated until a solid
  4. customcould be precipitated
  5. additionwas poured into hexane
  6. customthe precipitated solid was separated by filtration

Sources & evidence

ORD record
ord-d9c86f8ebb574201a1828d0d9adf8e43
Source dataset
uspto-grants-2004_02
Patent number
US06689899B2

Reaction notes

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