Hydrochloric Acid → Pentachlorophenyl Cyanoacetate

HRID 1980223Notes

Reaction equation

HRID 1980223 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].P(Cl)(Cl)(Cl)(Cl)Cl.Cl.[Cl:14][C:15]1[C:20](O)=[C:19]([Cl:22])[C:18]([Cl:23])=[C:17]([Cl:24])[C:16]=1[Cl:25]>ClCCl.C(OCC)C>[Cl:14][C:15]1[C:20]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[C:19]([Cl:22])[C:18]([Cl:23])=[C:17]([Cl:24])[C:16]=1[Cl:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 992PentachlorophenolHCID 9740Cyanoacetic acidHCID 24819Phosphorus pentachloride

Product 1

HCID 54054617Pentachlorophenyl Cyanoacetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

8.5 g (0.1 mole) of cyano acetic acid are dissolved in 350 ml. of ethylether and cooled to 0° C. 20.1 g. (0.1 mole) of phosphorus pentachloride are added. The cooling is stopped and the temperature is slowly raised to room temperature. When the HCl evolution ceases the solvent is distilled off in vacuo. The residue containing the formed cyanoacetic acid chloride and phosphoroxychloride is taken up in 50 ml. of dichloromethane and 26 g. (0.1 mole) of pentachlorophenol and 11 ml. (0.1 mole) of N,N'-dimethylaniline are added dropwise in 300 ml. of dichloromethane.

Workup

  1. distillationis distilled off in vacuo
  2. additionThe residue containing the formed cyanoacetic acid chloride and phosphoroxychloride

Sources & evidence

ORD record
ord-68ca663735ad40a19ca44ac3a7bcc0a4
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

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