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

HRID 839445Notes

Reaction equation

HRID 839445 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 chloride

Procedure

A mixture of 74.75 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 74.75 gm
  2. temperatureat reflux for ninety minutes
  3. customThe phosphorus oxychloride is removed by distillation in vacuo The residue
  4. washis washed with Skellysolve "B"
  5. customthe solvent removed by decantation
  6. customThe oily residue is recrystallized from benzene-cyclohexane
  7. customThere is obtained 58.2 gm

Sources & evidence

ORD record
ord-e21c572b2b5a45c79a213eff80fdf26c
Source dataset
uspto-grants-1978_06
Patent number
US04095028

Reaction notes

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