Diphenylacetonitrile → 2,2-Diphenylpent-4-ynenitrile

HRID 1657271Notes

Reaction equation

HRID 1657271 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.[CH2:16](Cl)[C:17]#[CH:18].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:10]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:18][C:17]#[CH:16])[C:8]#[N:9])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 6837DiphenylacetonitrileHCID 122213-Chloro-1-propyneHCID 14798Sodium Hydroxide

Product 1

HCID 108234172,2-Diphenylpent-4-ynenitrile

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

To a mixture of 2,2-diphenylacetonitrile (135.77 g), 2-propynyl chloride (52.35 g) and tetrabutylammonium hydrogen sulfate (0.51 g) was added dropwise 50% aqueous solution of sodium hydroxide (100 ml) at room temperature. After being stirred for 6 hours, the mixture was poured into water and extracted with diethyl ether. The extract was washed successively with diluted hydrochloric acid and brine, and evaporated in vacuo. The residue was distilled in vacuo to give 2,2-diphenyl-2-(2-propynyl)acetonitrile.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed successively with diluted hydrochloric acid and brine
  3. customevaporated in vacuo
  4. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-9e8596d2c6ab40dda01ab212c76a8428
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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