4-Chloro-3,5-dinitrobenzoic acid → 4-Chloro-3,5-dinitrobenzoyl chloride

HRID 236945

Reaction equation

HRID 236945 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].P(Cl)(Cl)(Cl)(Cl)[Cl:18]>>[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:5]([C:6]([Cl:18])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 83774-Chloro-3,5-dinitrobenzoic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 234515644-Chloro-3,5-dinitrobenzoyl chlorideYield 72%

Procedure

A mixture of 75.75 gm. (0.307 mole) of 4-chloro-3,5-dinitrobenzoic acid and 64.0 gm. (0.307 mole) of phosphorus pentachloride is heated at reflux for ninety minutes and cooled to room temperature. The phosphorus oxychloride is removed by distillation in vacuo. The residue is washed with Skellysolve "B" and the solvent removed by decantation. The oily residue is recrystallized from benzene-cyclohexane. There is obtained 58.2 gm (72%) of tan needles melting at 55°-57°.

Workup

  1. additionA mixture of 75.75 gm
  2. temperatureat reflux for ninety minutes
  3. customThe phosphorus oxychloride is removed by distillation in vacuo
  4. washThe residue is washed with Skellysolve "B"
  5. customthe solvent removed by decantation
  6. customThe oily residue is recrystallized from benzene-cyclohexane

Sources & evidence

ORD record
ord-6065e3b4817a411fa4daeb65713c57b8
Source dataset
uspto-grants-1979_06
Patent number
US04159278

Linked notes

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