Diphenylacetonitrile → alpha-Chloro-alpha-phenylbenzeneacetonitrile

HRID 436379Notes

Reaction equation

HRID 436379 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17]>O>[Cl:17][C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 6837DiphenylacetonitrileHCID 24819Phosphorus pentachloride

Product 1

HCID 11075152alpha-Chloro-alpha-phenylbenzeneacetonitrileYield 91.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25 g (0.13 m) of diphenylacetonitrile and 27 g (0.13 m) of phosphorus pentachloride is heated at 125° for 4 hours. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are washed with 10% hydrochloric acid, saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate. The solvent is evaporated to give 27 g of crude α-chlorodiphenylacetonitrile.

Workup

  1. temperatureis heated at 125° for 4 hours
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with 10% hydrochloric acid, saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-df1e971d0ae44b03838bb339bb9a61b1
Source dataset
uspto-grants-1977_02
Patent number
US04009021

Reaction notes

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