Pentachlorophenol → alpha-Cyano-phenylacetic acid pentachlorophenylester

HRID 1980227

Reaction equation

HRID 1980227 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].C1(N=C=NC2CCCCC2)CCCCC1.[Cl:28][C:29]1[C:34](O)=[C:33]([Cl:36])[C:32]([Cl:37])=[C:31]([Cl:38])[C:30]=1[Cl:39]>ClCCl>[Cl:28][C:29]1[C:34]([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:33]([Cl:36])[C:32]([Cl:37])=[C:31]([Cl:38])[C:30]=1[Cl:39]

Participants

5

Reactant 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 26403alpha-Cyanobenzeneacetic acid

Product 1

HCID 20402417alpha-Cyano-phenylacetic acid pentachlorophenylester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

8 g. (0.05 moles) of α-cyano-phenylacetic acid are dissolved in 80 ml. of dichloromethane. 10.3 g. (0.05 moles) of dicyclohexylcarbodiimide and 13 g. (0.05 moles) of pentachlorophenol are added dropwise dissolved in 50 ml. of dichloromethane. The mixture is stirred for 4 hours, cooled to 0° C. and the precipitated dicyclohexylurea is filtered. The filtered substance is washed twice on the filter with 15 ml. of dichloromethane. The combined organic layers are distilled off and the precipitated ester is taken up with 20 ml. of diisopropyl ether and the crystals are filtered, washed twice with diisopropyl ether and dried.

Workup

  1. dissolutiondissolved in 50 ml
  2. filtrationthe precipitated dicyclohexylurea is filtered
  3. washThe filtered substance is washed twice on the
  4. filtrationfilter with 15 ml
  5. distillationThe combined organic layers are distilled off
  6. filtrationof diisopropyl ether and the crystals are filtered
  7. washwashed twice with diisopropyl ether
  8. customdried

Sources & evidence

ORD record
ord-697caea644814226b08ef5af17886796
Source dataset
uspto-grants-1985_04
Patent number
US04508658

Linked notes

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