Hydrochloric Acid → alpha-Cyano-phenylacetic acid pentachlorophenylester

HRID 1980226

Reaction equation

HRID 1980226 reaction equation
[C:1]([CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5])#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[Cl:20][C:21]1[C:26](O)=[C:25]([Cl:28])[C:24]([Cl:29])=[C:23]([Cl:30])[C:22]=1[Cl:31].N1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.ClCCl>[Cl:20][C:21]1[C:26]([O:5][C:4](=[O:6])[CH:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:1]#[N:2])=[C:25]([Cl:28])[C:24]([Cl:29])=[C:23]([Cl:30])[C:22]=1[Cl:31]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 992PentachlorophenolHCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 26403alpha-Cyanobenzeneacetic acid

Product 1

HCID 20402417alpha-Cyano-phenylacetic acid pentachlorophenylester

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent2×

Procedure

8 g. (0.05 moles) of α-cyano-phenylacetic acid are dissolved in 80 ml. of dichloromethane, 10.2 g. (0.05 moles) of phosphorous pentachloride are added and the mixture is stirred for 2 hours at the boiling point of the dichloromethane. The reaction is completed when the hydrochloric acid evolution ceases. The solvent is distilled off and the residue containing the obtained acid chloride and phosphoroxychloride is taken up in carbontetrachloride and the solution is added dropwise to 13 g. (0.05 moles) of pentachlorophenol and 4 ml. (0.05 moles) of pyridine dissolved in 200 ml. of carbontetrachloride. The reaction mixture is cooled and the precipitated pyridine chlorohydrate is removed by washing twice with 50 ml. of water, dried, distilled off and the residue is distilled off with diisopropyl ether. The precipitated crystalline product is cooled and filtered. The α-cyanophenylacetic acid pentachlorophenyl ester is air-dried.

Workup

  1. distillationThe solvent is distilled off
  2. additionthe residue containing the obtained acid chloride and phosphoroxychloride
  3. additionthe solution is added dropwise to 13 g
  4. temperatureThe reaction mixture is cooled
  5. customthe precipitated pyridine chlorohydrate is removed
  6. washby washing twice with 50 ml
  7. dry with materialof water, dried
  8. distillationdistilled off
  9. distillationthe residue is distilled off with diisopropyl ether
  10. temperatureThe precipitated crystalline product is cooled
  11. filtrationfiltered
  12. dry with materialThe α-cyanophenylacetic acid pentachlorophenyl ester is air-dried

Sources & evidence

ORD record
ord-43ffbc2a2594471d80d70c227c2d8036
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Linked notes

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