Hydrochloric Acid → Benzeneacetonitrile, 2-chloro-α-(4-chlorophenyl)-4-nitro-

HRID 2219080Notes

Reaction equation

HRID 2219080 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[Cl:11].[OH-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]#[N:23])=[CH:17][CH:16]=1.Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O1CCCC1.O>[Cl:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[CH:21]([C:18]1[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=1)[C:22]#[N:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74431,2-Dichloro-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 18510711Benzeneacetonitrile, 2-chloro-α-(4-chlorophenyl)-4-nitro-Yield 0.1%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

) To a stirred and warm (40° C.) mixture of 1,2-dichloro-4-nitrobenzene (0,250 mol), 450 ml of NaOH solution 50%, 0,002 mol of N,N,N-triethylbenzenemethanaminium chloride and 225 ml of tetrahydrofuran is added dropwise a solution of 0,272 mol of 4-chlorobenzeneacetonitrile in 70 ml of tetrahydrofuran. Upon completion, stirring is continued for 5 hours at ±60° C. The reaction mixture is cooled and diluted with water. The whole is acidified with a hydrochloric acid solution and the product is extracted with Et2O. The extract is washed with water, dried, filtered and evaporated, yielding 80 g of 2-chloro-α-(4-chlorophenyl)-4-nitrobenzeneacetonitrile as an oily solution. (interm. 4)

Workup

  1. temperaturewarm
  2. stirringUpon completion, stirring
  3. temperatureThe reaction mixture is cooled
  4. extractionthe product is extracted with Et2O
  5. washThe extract is washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-463486d2536a432ca157dad7b949befd
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

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