Potassium Carbonate → 4-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

HRID 1248525Notes

Reaction equation

HRID 1248525 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.Br[CH:21]([CH3:30])[C:22]([O:28][CH3:29])=[CH:23][C:24]([O:26]C)=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:21]([CH3:30])[C:22]([O:28][CH3:29])=[CH:23][C:24]([OH:26])=[O:25])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129406134-[2-Chloro-4-(trifluoromethyl)phenoxy]phenolHCID 54279858Methyl 4-bromo-3-methoxypent-2-enoate

Product 1

HCID 538603484-[4-(2-Chloro-4-trifluoromethylphenoxy)phenoxy]-3-methoxy-2-pentenoic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(2-chloro-4-trifluoromethylphenoxy) phenol (6.9 mmol.), methyl 4-bromo-3-methoxy-2-pentenoate (8.9 mmol.) and potassium carbonate (1.5 equis.) in acetone (15 ml.) is refluxed for 48 hours. After filtration, the filtrate was concentrated and the residue chromatographed on silica gel using 20% ethylacetate/hexane to give the methyl ester of 4-[4-(2-chloro-4-trifluoromethylphenoxy) phenoxy]-3-methoxy-2-pentenoic acid.

Workup

  1. temperatureis refluxed for 48 hours
  2. filtrationAfter filtration
  3. concentrationthe filtrate was concentrated
  4. customthe residue chromatographed on silica gel using 20% ethylacetate/hexane

Sources & evidence

ORD record
ord-6539f3e0353640e7b7d3f46fb93589b9
Source dataset
uspto-grants-1985_06
Patent number
US04525205

Reaction notes

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