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

HRID 2286680Notes

Reaction equation

HRID 2286680 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:27](Br)[CH3:28])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].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:27]([CH3:28])[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 12922552Ethyl 3,4-dibromopentanoate

Product 1

HCID 156921Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a reactor, 30 g of ethanol was charged and 12.7 g (0.05 mole) of 4-(4-trifluoromethylphenoxy)phenol, 15.8 g (0.055 mole) of ethyl 3,4-dibromopentanoate, 8.7 g (0.063 mole) of potassium carbonate were charged. They were refluxed for 6 hours to react them. After the reaction, ethanol was distilled off from the reaction mixture and then 50 ml of toluene was added to the resulting mixture, and resulting solution was washed with water and then, the organic phase was washed with 5% hydrochloric acid and with water and then ethyl 3,4-dibromopentanoate and a lower boiling by-products were distilled off at 100° C. under a reduced pressure of 0.02-0.05 mmHg to obtain 15.6 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate (nD20 1.5175). The yield was 82.0%. The same process was repeated to obtain same compound except using ethyl 3,4-dichloropentanoate 10.9 g (0.055 mole) instead of ethyl 3,4-dibromopentanoate 15.8 g (0.055 mole). The yield was 73.6%.

Workup

  1. temperatureThey were refluxed for 6 hours
  2. customto react them
  3. distillationwas distilled off from the reaction mixture
  4. addition50 ml of toluene was added to the resulting mixture
  5. customresulting solution
  6. washwas washed with water
  7. washthe organic phase was washed with 5% hydrochloric acid and with water
  8. distillationethyl 3,4-dibromopentanoate and a lower boiling by-products were distilled off at 100° C. under a reduced pressure of 0.02-0.05 mmHg

Sources & evidence

ORD record
ord-1f9d297e08914e4691569c3e88bf165d
Source dataset
uspto-grants-1981_05
Patent number
US04267317

Reaction notes

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