Acetic Acid → 3-(2-Benzoyl-4-chlorophenyl)prop-2-enenitrile

HRID 1903617Notes

Reaction equation

HRID 1903617 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]=[CH:16][C:17]#[N:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(=[O:24])C.C(O)C>O.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[CH:15]=[CH:16][C:17]#[N:18])(=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6344DichloromethaneHCID 545603803-(2-Benzyl-4-chlorophenyl)prop-2-enenitrile

Product 1

HCID 543140203-(2-Benzoyl-4-chlorophenyl)prop-2-enenitrile

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalyst2×HCID 962WaterSolvent

Procedure

A mixture of 28.8 g (0.14 mol) of 3-[2-benzyl-4-chlorophenyl]-2-propenenitrile, 50 g (0.5 mol) of chromium trioxide, 100 ml of methylene chloride, and 300 ml of acetic acid was stirred at room temperature overnight. The excess chromium trioxide was discharged by the slow addition of 30 ml of ethanol. The mixture was diluted with 800 ml of water and extracted with 500 ml of ether. The ether solution was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride. The ether solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a yellow oil which was used without further purification.

Workup

  1. extractionextracted with 500 ml of ether
  2. washThe ether solution was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride
  3. dry with materialThe ether solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure
  5. customto give a yellow oil which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-26938e1d16094e70873d8b1f70baa312
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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