Hydrochloric Acid → Pentachlorophenyl Cyanoacetate

HRID 1980222Notes

Reaction equation

HRID 1980222 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].[Cl:7][C:8]1[C:13](O)=[C:12]([Cl:15])[C:11]([Cl:16])=[C:10]([Cl:17])[C:9]=1[Cl:18].O=P(Cl)(Cl)Cl.Cl>>[Cl:7][C:8]1[C:13]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[C:12]([Cl:15])[C:11]([Cl:16])=[C:10]([Cl:17])[C:9]=1[Cl:18]

Participants

5

Reactant 4

HCID 313Hydrochloric Acid2×HCID 992PentachlorophenolHCID 9740Cyanoacetic acidHCID 24813Phosphorus oxychloride

Product 1

HCID 54054617Pentachlorophenyl Cyanoacetate

Procedure

17 g. (0.2 moles) of cyanoacetic acid are mixed thorougly with 53.2 g. (0.2 moles) of pentachlorophenol, and 19.0 ml. (0.2 moles) of phosphoroxychloride are added dropwise. The obtained mixture is heated slowly on an oil-bath, until the inner temperature rises to 85° to 90° C. and the solid melts under intensive evolution of HCl. The homogeneous melt is heated until the hydrochloric acid evolution ceases. In the meantime the first cyanoacetic acid pentachlorophenyl ester precipitate is obtained. When the hydrochloric acid evolution ceases, the system is cooled and dissolved in 500 ml. of dichloromethane, washed 3 times with 100 ml. of water, treated with decolorizing charcoal, dried and evaporated. Diisopropyl ether is added. Cyanoacetic acid pentachlorophenyl ester precipitates in the form of crystals.

Workup

  1. temperatureThe obtained mixture is heated slowly on an oil-bath, until the inner temperature
  2. customrises to 85° to 90° C.

Sources & evidence

ORD record
ord-47d2226207684c0e9e06b2538d33f76c
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

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