Acetic Acid → HCID 21327871, compound

HRID 614521Notes

Reaction equation

HRID 614521 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:3]=1N.C(O)(=O)C.N([O-])=O.[Na+].[CH:21]([CH:23]=[CH2:24])=[O:22].[ClH:25]>O.CC(C)=O.Cl[Cu]>[Cl:25][CH:23]([CH2:24][C:3]1[CH:5]=[C:6]([C:9]([F:12])([F:11])[F:10])[CH:7]=[CH:8][C:2]=1[Cl:1])[CH:21]=[O:22]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 7847AcroleinHCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 21327871HCID 21327871, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

195.5 g (1 mole) of 2-chloro-5-trifluoromethylaniline are added to a mixture of 280 ml of concentrated HCl and 280 ml of acetic acid. After the mixture has been cooled to 0° C., 75 g of NaNO2 dissolved in 150 ml of water are slowly added to the mixture, the temperature being maintained between 0° and 3° C. At the same temperature, a mixture of 5 g of CaO and 60 g of acrolein dissolved in 250 ml of acetone is then introduced. A solution of 1 g of CuCl in 20 ml of concentrated HCl is then added; the temperature is maintained between 5° and 10° C. The evolution of nitrogen ceases after a reaction time of 1 hour. The α-chloro-β-(2-chloro-5-trifluoromethyl-phenyl)propionaldehyde is extracted by ether and washed in water. After drying and removal of the solvent the product is distilled at a reduced pressure. 135 g, corresponding to a 50% yield, of a slightly yellowish oil distilling between 98° and 100° C. at a pressure of 0.5 mm are obtained.

Workup

  1. additionare slowly added to the mixture
  2. temperaturethe temperature being maintained between 0° and 3° C
  3. additionis then introduced
  4. temperaturethe temperature is maintained between 5° and 10° C
  5. customafter a reaction time of 1 hour
  6. extractionThe α-chloro-β-(2-chloro-5-trifluoromethyl-phenyl)propionaldehyde is extracted by ether
  7. washwashed in water
  8. customAfter drying
  9. customremoval of the solvent the product
  10. distillationis distilled at a reduced pressure
  11. distillation135 g, corresponding to a 50% yield, of a slightly yellowish oil distilling between 98° and 100° C. at a pressure of 0.5 mm
  12. customare obtained

Sources & evidence

ORD record
ord-73fa87d25a5340ef9d0247661f097e05
Source dataset
uspto-grants-1979_03
Patent number
US04145362

Reaction notes

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