Hydrochloric Acid → 2-[4-(trifluoromethyl)phenoxy]propanoic Acid

HRID 1704146Notes

Reaction equation

HRID 1704146 reaction equation
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[CH:6]=[CH:7][C:8]([OH:11])=[CH:9][CH:10]=1.[H][H].Cl.Br[CH:18]([CH3:22])[C:19]([OH:21])=[O:20]>CN(C)C=O.O>[F:3][C:4]([F:12])([F:13])[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH:18]([CH3:22])[C:19]([OH:21])=[O:20])=[CH:9][CH:10]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 117292-Bromopropionic acidHCID 24758Sodium hydrideHCID 678744-(Trifluoromethyl)phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 37536562-[4-(trifluoromethyl)phenoxy]propanoic AcidYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of 12 g of sodium hydride-oil dispersion (57%) in 100 ml of N,N-dimethylformamide is added 21 g of α,α,α-trifluoro-p-cresol in 10 ml of dimethylformamide and 24 g of 2-bromopropionic acid. After hydrogen evolution, the mixture is heated at 90° C. for 14 hrs. The mixture is cooled, diluted with 100 ml of water, acidified with hydrochloric acid and extracted with ether. The ether extracts are dried (MgSO4) and concentrated to give 23 g of product. A 3.5 g sample is chromatographed over silica gel with solvent hexane-ether-acetic acid (80:20:1) to give 2.3 g of white crystals. Recrystallization from hexane gives crystals, mp 81°-82° C.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with ether
  3. dry with materialThe ether extracts are dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0373545a24f14bfa93a93e41a1527665
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

Loading…