Phenol → 2-{4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenoxy}propanoic acid

HRID 1446896Notes

Reaction equation

HRID 1446896 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.C(=O)([O-])[O-].[K+].[K+].Cl[CH:27]([CH3:31])[C:28]([OH:30])=[O:29].C1(O)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.O1CCOCC1>[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:27]([CH3:31])[C:28]([OH:30])=[O:29])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 117342-Chloropropionic acidHCID 129406134-[2-Chloro-4-(trifluoromethyl)phenoxy]phenol

Product 1

HCID 129060172-{4-[2-Chloro-4-(trifluoromethyl)phenoxy]phenoxy}propanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

28.9 g of 4-(2-chloro-4-trifluoromethylphenoxy)phenol was added to 50 ml of dioxane, and with stirring at 30° to 40° C., 13.8 g of potassium carbonate was added. The mixture was heated to 40° to 60° C., and 10.8 g of α-chloropropionic acid was added. The reaction was performed for 4 hours. The disappearance of the starting phenol was confirmed by gas chromatography, and the reaction product was poured into a suitable amount of water. Sodium carbonate was added to transfer the final product into the aqueous phase. The oily phase was separated and removed, and then hydrochloric acid was added to afford 20 g of a solid precipitate. The final product obtained had a melting point of 90° to 92° C.

Workup

  1. temperatureThe mixture was heated to 40° to 60° C.

Sources & evidence

ORD record
ord-79900fee76d5401aa8e7660e00309c50
Source dataset
uspto-grants-1982_02
Patent number
US04314069

Reaction notes

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