Ethyl 2-chloropropionate → Ethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoate

HRID 1105728Notes

Reaction equation

HRID 1105728 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.Cl[CH:20]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(C(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]([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10807Ethyl 2-chloropropionateHCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenol

Product 1

HCID 631921Ethyl 2-[4-[4-(trifluoromethyl)phenoxy]phenoxy]propanoateYield 54%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 73.5 g of 4-(4-trifluoromethylphenoxy)phenol and 49.2 g of ethyl α-chloropropionate and 100 g of potassium carbonate were added to 100 ml of methyl ethyl ketone, and the mixture was heated. With stirring, the reaction was performed for 10 hours at the reflux temperature (80° to 85° C.). Inorganic salts were separated from the reaction product by filtration. The filtrate was evaporated and dried. The resulting ester was extracted with chloroform, and washed with water. The chloroform was distilled off to afford 55 g of the final product (yield: 54%). The final product had a boiling point of 176° to 185° C./3 mmHg.

Workup

  1. temperaturethe mixture was heated
  2. customInorganic salts were separated from the reaction product by filtration
  3. customThe filtrate was evaporated
  4. customdried
  5. extractionThe resulting ester was extracted with chloroform
  6. washwashed with water
  7. distillationThe chloroform was distilled off

Sources & evidence

ORD record
ord-0180b70e8a9e4fb0a1e4ae74dd24f9d1
Source dataset
uspto-grants-1982_01
Patent number
US04309562

Reaction notes

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