Sulfuric Acid → (4-Chlorophenyl)phenylacetonitrile

HRID 1781495Notes

Reaction equation

HRID 1781495 reaction equation
[C:1](#[N:10])[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)O.S(=O)(=O)(O)O.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([CH:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:1]#[N:10])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7964ChlorobenzeneHCID 10758Mandelonitrile

Product 1

HCID 4414244(4-Chlorophenyl)phenylacetonitrileYield 42.1%

Procedure

To a mixture of mandelonitrile (5 g) and chlorobenzene (15.7 g) was added sulfuric acid (9.8 ml) dropwise while the temperature of the mixture was maintained at 5°-10° C. After completion of dropwise addition, the mixture was stirred for another 1.5 hours. This reaction mixture was poured in ice-water and the syrup that had separated out was extracted into ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was purified by silica gel column chromatography to provide the title compound (3.6 g) as pale yellow syrup.

Workup

  1. temperaturewas maintained at 5°-10° C
  2. additionAfter completion of dropwise addition
  3. customthe syrup that had separated out
  4. extractionwas extracted into ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe group was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-58636e593d6041a8ad292a9becfec4cf
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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