Diethyl Ether → HCID 53835796, compound

HRID 1701349Notes

Reaction equation

HRID 1701349 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:7].[C-:18]#[N:19].[K+].CCOCC>O1CCOCC1.O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:4]=[C:3]([CH2:2][C:18]#[N:19])[CH:17]=[CH:16][CH:15]=2)=[O:7])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 9032Potassium CyanideHCID 136496533-(4-Chlorobenzoyl)benzyl bromide

Product 1

HCID 53835796HCID 53835796, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 17 g of 3-bromomethyl-4'-chlorobenzophenone in 75 cc of dioxane at 70° C. was added to the solution of 26.5 g of potassium cyanide in 75 cc of water and the mixture was refluxed with stirring for 6 hours. After cooling, 500 cc of ether were added to the mixture and the aqueous phase was decanted off. The organic phase was washed with water until the wash waters were neutral, dried over magnesium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure. The residue was crystallized from methanol to obtain 9.61 g of 3-p-chlorobenzoyl phenyl acetonitrile melting at 86° to 90° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureAfter cooling
  3. customthe aqueous phase was decanted off
  4. washThe organic phase was washed with water until the wash waters
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated carbon
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-1ddc5f67f04f4705a8040dadd4cad108
Source dataset
uspto-grants-1980_03
Patent number
US04192890

Reaction notes

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