Acetic Acid → (2,6-Dichlorophenyl)acetonitrile

HRID 743137Notes

Reaction equation

HRID 743137 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]=O.C(O)(=O)C.[C-:15]#[N:16].[K+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:15]#[N:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67372,6-DichlorobenzaldehydeHCID 9032Potassium Cyanide

Product 1

HCID 76678(2,6-Dichlorophenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.25 parts of (2,6-dichlorophenyl)methanone, 4.08 parts of intermediate 8 and 105 parts of acetic acid was stirred for 2 hours at room temperature. There were added 1.96 parts of potassium cyanide and stirring was continued for 20 hours. The reaction mixture was poured into water and the product was extracted with dichloromethane. The extract was washed with NaOH (10%) and water, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 80:20). The eluent of the desired fraction was evaporated and the residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 4.28 parts (49.3%) of (±)-α-[2-acetyl-5-ethylphenyl)amino]-2,6-dichlorobenzeneacetonitrile; mp. 111.3° C. (interm. 9).

Workup

  1. stirringstirring
  2. waitwas continued for 20 hours
  3. extractionthe product was extracted with dichloromethane
  4. washThe extract was washed with NaOH (10%) and water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /hexane 80:20)
  9. customThe eluent of the desired fraction was evaporated
  10. customthe residue was crystallized from 2,2'-oxybispropane
  11. filtrationThe product was filtered off
  12. customdried

Sources & evidence

ORD record
ord-a2dac17f1b06429fbf57f31ae2b54ec6
Source dataset
uspto-grants-1996_09
Patent number
US05556886

Reaction notes

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