Hydrochloric Acid → 3,5-Dinitrobenzoyl chloride

HRID 380719Notes

Reaction equation

HRID 380719 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-94448e8b87084c39ae84e619c07fa7d8
Source dataset
uspto-grants-2001_10
Patent number
US06303742B1

Reaction notes

Loading…