Chloroacetonitrile → HCID 23350111, compound

HRID 263079Notes

Reaction equation

HRID 263079 reaction equation
Cl[CH2:2][C:3]#[N:4].[Na].[Cl:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>C(O)C>[Cl:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:2][C:3]#[N:4])=[CH:14][CH:13]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 5360545SodiumHCID 123461204-(4-Chlorophenoxy)phenol

Product 1

HCID 23350111HCID 23350111, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.78 g (0.0500 mol) of chloroacetonitrile in 10 ml of anhydrous ethanol is run over the course of 20 minutes into a solution of 1.04 g (0.0453 mol) of sodium and 10 g (0.0453 mol) of p-(p-chlorophenoxy)-phenol in 50 ml of anhydrous ethanol and the mixture is then heated to the reflux temperature for 4 hours. It is evaporated to dryness under reduced pressure and the residue is dissolved in diethyl ether, which is washed with water and with dilute sodium hydroxide solution. After drying over dry sodium sulphate and evaporating the solvent from the organic phase, 12 g of an orange-coloured oil are obtained. Purification of this oil by distillation under reduced pressure gives 9.5 g of a limpid pale yellow oil which is insoluble in water.

Workup

  1. temperaturethe mixture is then heated to the reflux temperature for 4 hours
  2. customIt is evaporated to dryness under reduced pressure
  3. dissolutionthe residue is dissolved in diethyl ether
  4. washwhich is washed with water and with dilute sodium hydroxide solution
  5. dry with materialAfter drying over dry sodium sulphate
  6. customevaporating the solvent from the organic phase, 12 g of an orange-coloured oil
  7. customare obtained
  8. customPurification of this oil
  9. distillationby distillation under reduced pressure

Sources & evidence

ORD record
ord-22e92a16118340d3b8fc875817ad0798
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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