Benzene → HCID 21483200, compound

HRID 1415579Notes

Reaction equation

HRID 1415579 reaction equation
[OH-].[K+].Cl[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH2:21][C:22]#[N:23].C1C=CC=CC=1>N1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[CH:21]([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1)[C:22]#[N:23]

Participants

6

Reactant 4

HCID 241BenzeneHCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 805662,4-Dichlorophenylacetonitrile

Product 1

HCID 21483200HCID 21483200, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent3×

Conditions

Temperature
-5 °C

Procedure

To a solution of 39 parts of potassium hydroxide in 39 parts of pyridine is added a solution of 17 parts of 1-chloro-4-nitrobenzene in 46 parts of pyridine. The whole is cooled to -5° C and there is added dropwise a solution of 22 parts of 2,4-dichlorobenzeneacetonitrile in pyridine, while still cooling at -5° C. Upon completion, stirring is continued for 10 hours at 0° C. After the addition of 90 parts of benzene, the product is precipitated. It is filtered off, washed on the filter with benzene and taken up in water. The aqueous mixture is treated with acetic acid, whereupon the product is separated as an oil. The latter is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is crystallized from a mixture of methanol, 2,2' -oxybispropane, petroleumether and trichloromethane, yielding 2,4-dichloro-α-(4-nitrophenyl)benzeneacetonitrile; mp. 81°- 82.5° C.

Workup

  1. temperaturewhile still cooling at -5° C
  2. customthe product is precipitated
  3. filtrationIt is filtered off
  4. washwashed on the
  5. filtrationfilter with benzene
  6. additionThe aqueous mixture is treated with acetic acid, whereupon the product
  7. customis separated as an oil
  8. extractionThe latter is extracted with methylbenzene
  9. customThe extract is dried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is crystallized from a mixture of methanol, 2,2' -oxybispropane, petroleumether and trichloromethane

Sources & evidence

ORD record
ord-ea7c520f7e624c129f2231fd3b718341
Source dataset
uspto-grants-1977_01
Patent number
US04005218

Reaction notes

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