Hydrochloric Acid → p-(1-Trifluoromethylheptyloxy)iodobenzene

HRID 485986Notes

Reaction equation

HRID 485986 reaction equation
Cl.[F:2][C:3]([F:20])([F:19])[CH:4]([O:11][C:12]1[CH:18]=[CH:17][C:15](N)=[CH:14][CH:13]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N([O-])=O.[Na+].[I-:25].[K+]>O>[F:2][C:3]([F:20])([F:19])[CH:4]([O:11][C:12]1[CH:18]=[CH:17][C:15]([I:25])=[CH:14][CH:13]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 15123948p-(1-Trifluoromethylheptyloxy)-anilineHCID 23668193Sodium Nitrite

Product 1

HCID 15123949p-(1-Trifluoromethylheptyloxy)iodobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To 200 ml of water containing 25 g of 36% hydrochloric acid, were added 6.7 g of oa p-(1-trifluoromethyl-heptyloxy)-aniline, and cooled to a temperature below 5° C., followed by adding thereto dropwise 1.7 g of sodium nitrite dissolved in 10 ml of water. After the addition was over, stirring was continued for an hour, and then 20 g of potassium iodide dissolved in 20 ml of water were added thereto, followed by putting back the temperature gradually to room temperature and stirring was continued until no evolution of nitrogen was observed. After completion of the reaction, the product was extracted with hexane. The hexane phase was washed subsequently with water, an aqueous solution of sodium hydrogen sulfite and then water, followed by distilling off the hexane to obtain 77 g of oily oa p-(1-trifluoromethylheptyloxy)iodobenzene.

Workup

  1. temperaturecooled to a temperature below 5° C.
  2. additionby adding
  3. additionAfter the addition
  4. waitwas continued for an hour
  5. additionwere added
  6. customgradually to room temperature
  7. stirringstirring
  8. customAfter completion of the reaction
  9. extractionthe product was extracted with hexane
  10. washThe hexane phase was washed subsequently with water
  11. distillationby distilling off the hexane

Sources & evidence

ORD record
ord-be1fa85db660458dbe5a141cf136221e
Source dataset
uspto-grants-1994_03
Patent number
US05290478

Reaction notes

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