Ethylene Glycol → 2,3,4,5-Tetrachloro-6-(2-hydroxyethoxy)benzonitrile

HRID 1973159Notes

Reaction equation

HRID 1973159 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[C:5]([Cl:11])=[C:4]([Cl:12])[C:3]=1[Cl:13].[CH2:14]([OH:17])[CH2:15][OH:16].[H-].[Na+].O>O1CCCC1>[OH:16][CH2:15][CH2:14][O:17][C:2]1[C:7]([C:8]#[N:9])=[C:6]([Cl:10])[C:5]([Cl:11])=[C:4]([Cl:12])[C:3]=1[Cl:13]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 24758Sodium hydrideHCID 30363Pentachlorobenzonitrile

Product 1

HCID 214930642,3,4,5-Tetrachloro-6-(2-hydroxyethoxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To solution of 34.4 grams of pentachlorobenzonitrile in tetrahydrofuran was added a mixture of 8.0 grams ethylene glycol, 8.0 grams of a 50% sodium hydride-mineral oil dispersion and 250 ml tetrahydrofuran. The resulting reaction mixture was heated at reflux for one hour and then poured into a large volume of water. Filtration afforded an almost colorless solid which was dissolved in tetrahydrofuran. Treatment with magnesium sulfate followed by filtration and removal of the solvent gave rise to beta-hydroxyethoxy-tetrachlorobenzonitrile. This material is identical basis both nmr and infrared spectral data to the product formed from the reaction of tetrachlorocyanophenol with ethylene oxide as set forth below.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureat reflux for one hour
  4. filtrationFiltration
  5. customafforded an almost colorless solid which
  6. filtrationTreatment with magnesium sulfate followed by filtration and removal of the solvent

Sources & evidence

ORD record
ord-24a069032c104c10a4f342ca57085ced
Source dataset
uspto-grants-1976_12
Patent number
US03996258

Reaction notes

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