Potassium Carbonate → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate

HRID 126972Notes

Reaction equation

HRID 126972 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]([CH3:28])[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[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:20]([CH3:28])[CH:21]=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 53952747Ethyl 4-bromopent-2-enoate

Product 1

HCID 156921Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoateYield 73.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a reactor, 100 ml of ethanol was charged and 95.3 g (0.375 mole) of 4-(4-trifluoromethylphenoxy)phenol, 85.4 g (0.412 mole) of ethyl 4-bromo-2-pentenoate and 39.0 g (0.281 mole) of potassium carbonate were added. The mixture was refluxed with stirring for 6 hours to react them. Ethanol was distilled off and 100 ml of chlorobenzene and 100 ml of water were added and the mixture was stirred at the room temperature for 30 minutes. The water phase was separated and the organic phase was washed with 5% hydrochloric acid and with water and then, chlorobenzene, ethyl 4-bromo-2-pentenoate and low boiling by-products were distilled off under a reduced pressure to obtain 10.47 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate. The yield was 73.5%.

Workup

  1. temperatureThe mixture was refluxed
  2. customto react them
  3. distillationEthanol was distilled off
  4. addition100 ml of chlorobenzene and 100 ml of water were added
  5. stirringthe mixture was stirred at the room temperature for 30 minutes
  6. customThe water phase was separated
  7. washthe organic phase was washed with 5% hydrochloric acid and with water
  8. distillationchlorobenzene, ethyl 4-bromo-2-pentenoate and low boiling by-products were distilled off under a reduced pressure

Sources & evidence

ORD record
ord-200e2e8618bd44999f969e0b42e698f7
Source dataset
uspto-grants-1981_03
Patent number
US04254262

Reaction notes

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