Pentachlorophenol → Pentachlorophenyl Cyanoacetate

HRID 1980224Notes

Reaction equation

HRID 1980224 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=[O:5])#[N:2].C1(N=C=NC2CCCCC2)CCCCC1.[Cl:22][C:23]1[C:28](O)=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33]>ClCCl>[Cl:22][C:23]1[C:28]([O:5][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 9740Cyanoacetic acidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 54054617Pentachlorophenyl Cyanoacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

17 g. (0.2 moles) of cyanoacetic acid are dissolved in 150 ml. of dichloromethane and 40 g. (0.2 moles) of dicyclohexylcarbodiimide and 52 g. (0.2 moles) of pentachlorophenol dissolved in 200 ml. of dichloromethane are added dropwise at room temperature. The mixture is stirred for 4 hours at room temperature. The mixture is cooled to 0° C. and the precipitated dicyclohexylcarbodiimide is filtered and the solvent is distilled off. The residue is taken up in diisopropyl ether, filtered and dried.

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. filtrationthe precipitated dicyclohexylcarbodiimide is filtered
  3. distillationthe solvent is distilled off
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-8e869d5b0ad94ce5a5d926cf3a362354
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Reaction notes

Loading…