Potassium Carbonate → 4-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acid

HRID 2286681Notes

Reaction equation

HRID 2286681 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH:20]([CH:25](Br)[CH3:26])[CH2:21][C:22]([OH:24])=[O:23].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH:25]([CH3:26])[CH:20]=[CH:21][C:22]([OH:24])=[O:23])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 150899703,4-Dibromopentanoic acid

Product 1

HCID 1577944-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acidYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a reactor, 30 g of tetrahydrofuran was charged and 12.7 g (0.05 mole) of 4-(4-trifluoromethylphenoxy)phenol, 14.3 g (0.055 mole) of 3,4-dibromopentanoic acid and 16.6 g of potassium carbonate were charged. They were refluxed for 6 hours to react them. After the reaction, tetrahydrofurane was distilled off from the reaction mixture and then 50 ml of chlorobenzene was added to the resulting mixture and then conc. hydrochloric acid was added to the resulting mixture with stirring to be acidic and then, the water phase was separated and the organic phase washed with water and then, chlorobenzene and low boiling by-products were distilled off at 100° C. under a reduced pressure (0.02-0.05 mmHg) to obtain 13.2 g of 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoic acid. (nD20 1.5284). The yield was 75%.

Workup

  1. temperatureThey were refluxed for 6 hours
  2. customto react them
  3. distillationwas distilled off from the reaction mixture
  4. addition50 ml of chlorobenzene was added to the resulting mixture
  5. additionconc. hydrochloric acid was added to the resulting mixture
  6. customthe water phase was separated
  7. washthe organic phase washed with water
  8. distillationchlorobenzene and low boiling by-products were distilled off at 100° C. under a reduced pressure (0.02-0.05 mmHg)

Sources & evidence

ORD record
ord-ef870c34523649ba94b5e2223d72929e
Source dataset
uspto-grants-1981_05
Patent number
US04267317

Reaction notes

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