Ethanol → HCID 53671598, compound

HRID 2352623Notes

Reaction equation

HRID 2352623 reaction equation
[CH2:1]([N:5](C(=O)C(Cl)Cl)[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1)[CH:2]=[CH:3][CH3:4].C(O)C.[OH-].[K+]>O>[CH2:1]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:13])([F:14])[F:15])[CH:7]=1)[CH:2]=[CH:3][CH3:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 53840275HCID 53840275, compound

Product 1

HCID 53671598HCID 53671598, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

64.64 grams (g) (0.198 mole) of N-crotyl-m-trifluoromethyl dichloroacetanilide and 300 milliliters (mL) of absolute ethanol were added to a round-bottomed flask, and stirred at room temperature, followed by the addition of 14.39 g of potassium hydroxide in 20 mL of water dropwise over a period of 10 minutes. After the addition was complete, the reaction mixture solidified with the precipitation of potassium dichloroacetate. The flask was swirled by hand to break up the solidified cake and stirring allowed to continue for an additional 18 hours. At the end of this time, 250 mL of ethylacetate was added and the mixture filtered. The solvent was then removed in vacuo to yield a pale orange-yellow semisolid. This was partitioned between 300 mL of ethylacetate and 300 mL of water and the layers were separated. The organic layer was washed one time with 200 mL of water and one time with 200 mL of a saturated sodium chloride solution. The organic layer was then dried with sodium sulfate and the solvent removed in vacuo to yield a yellow-orange material that was distilled at aspirator pressure to yield 36.6 g (86%) of product, N-crotyl-m-trifluoromethyl aniline.

Workup

  1. additionAfter the addition
  2. customthe reaction mixture solidified with the precipitation of potassium dichloroacetate
  3. stirringstirring
  4. additionAt the end of this time, 250 mL of ethylacetate was added
  5. filtrationthe mixture filtered
  6. customThe solvent was then removed in vacuo
  7. customto yield a pale orange-yellow semisolid
  8. customThis was partitioned between 300 mL of ethylacetate and 300 mL of water
  9. customthe layers were separated
  10. washThe organic layer was washed one time with 200 mL of water and one time with 200 mL of a saturated sodium chloride solution
  11. dry with materialThe organic layer was then dried with sodium sulfate
  12. customthe solvent removed in vacuo
  13. customto yield a yellow-orange material that
  14. distillationwas distilled at aspirator pressure

Sources & evidence

ORD record
ord-b9344d750fec45a98df2ed8de9908c2d
Source dataset
uspto-grants-1989_10
Patent number
US04877880

Reaction notes

Loading…