Hydrochloric Acid → 4-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acid

HRID 2286679Notes

Reaction equation

HRID 2286679 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+].Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O.C1(C)C=CC=CC=1>[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

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 150899703,4-Dibromopentanoic acid

Product 1

HCID 1577944-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acidYield 84.2%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In a reactor, 15 g of toluene and 15 g of water was charged in a reactor and then, 12.7 g (0.05 mole) of 4-(4-trifluoromethylphenoxy)phenol, 14.3 g (0.055 mole) of 3,4-dibromopentanoic acid, 16.6 g (0.12 mole) of potassium carbonate and 0.23 g (0.001 mole) of triethylbenzylammonium chloride were added. They were refluxed for 6 hours to react them and then, conc. hydrochloric acid was added to the reaction mixture with stirring to be acidic and then, the water phase was separated and the organic phase was washed with water and then, toluene and low boiling by-products were distilled off at 100° C. under a reduced pressure (0.02-0.05 mmHg) to obtain 14.8 g of 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoic acid (nD20 1.5284). The yield was 84.2%.

Workup

  1. temperatureThey were refluxed for 6 hours
  2. customto react them
  3. customthe water phase was separated
  4. washthe organic phase was washed with water
  5. distillationtoluene 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-d1e264ad0a604b07af5eb375d1ccca6f
Source dataset
uspto-grants-1981_05
Patent number
US04267317

Reaction notes

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