Chloride → (4-methoxyphenyl)(phenyl)acetonitrile

HRID 369921Notes

Reaction equation

HRID 369921 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH:7](Cl)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C-:17]#[N:18].[K+].[Cl-]>CC#N.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:17]#[N:18])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 312ChlorideHCID 9032Potassium CyanideHCID 5222586731-11-9

Product 1

HCID 233327(4-methoxyphenyl)(phenyl)acetonitrileYield 96.6%

Reagents, catalysts & solvents 2

HCID 26541Dibenzo-18-crown-6CatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of p-methoxybenzhydryl chloride (27.00 g, 0.116 mol) in dry CH3CN (200 mL) was added dibenzo-18-crown-6 (2.12 g) followed by dry KCN (8.02 g, 0.123 mol), and the stirred mixture was refluxed for 66 h. After this time, the reaction mixture was cooled to room temperature and the solid was removed by filtration. The filtrate was evaporated under vacuum. The resulting solid was dissolved in CH2Cl2 (50 mL) and the solution flushed through a silica gel column (230-400 mesh, 60 g) using CH2Cl2. The eluent was evaporated and the residue was titurated with heptane to precipitate the product. The precipitate was collected and washed with heptane to give a solid. 1H--NMR analysis of this solid showed that it was a mixture of starting chloride and product. Therefore, the heptane filtrates were evaporated and the solids were recombined, giving a total of 25.03 g of material. This solid was reacted again as described above, except that the reflux period was extended 48 h. Afterwards, the reaction mixture was worked up as described above to give the title nitrile (18.56 g, 72%) as a yellowish white solid. The structure was confirmed by 1H--NMR in CDCl3.

Workup

  1. temperaturethe stirred mixture was refluxed for 66 h
  2. customthe solid was removed by filtration
  3. customThe filtrate was evaporated under vacuum
  4. dissolutionThe resulting solid was dissolved in CH2Cl2 (50 mL)
  5. customthe solution flushed through a silica gel column (230-400 mesh, 60 g)
  6. customThe eluent was evaporated
  7. customto precipitate the product
  8. customThe precipitate was collected
  9. washwashed with heptane
  10. customto give a solid
  11. customTherefore, the heptane filtrates were evaporated

Sources & evidence

ORD record
ord-9552d5f56aa949f983e5518d29e9887d
Source dataset
uspto-grants-2000_10
Patent number
US06140137

Reaction notes

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