Potassium Hydroxide → HCID 21511432, compound

HRID 1576579Notes

Reaction equation

HRID 1576579 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11].I[C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1>[Cu].O>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[O:11][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:23])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 1230512,4-DifluorophenolHCID 152255732-(4-Iodophenyl)propanoic acid

Product 1

HCID 21511432HCID 21511432, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 962WaterSolvent

Procedure

Potassium hydroxide (3.4 g.) was fused at 180°C. with water (1 ml.), and 2,4-difluorophenol (5.2 g.) added. 2-(4-Iodophenyl)propionic acid (5.5 g.) and copper bronze (0.2 g.) were then added to the melt, and the resulting mixture was stirred at 160°-170°C. for 2 hours. The cooled solid was extracted with methylene chloride containing a little dilute hydrochloric acid, filtered, and the solution extracted with dilute potassium carbonate solution. The aqueous extract was washed with ether and acidified with dilute hydrochloric acid; the resulting oil was isolated in ether and evaporated to dryness. The resulting solid was purified by preparative layer chromatography using 5% acetic acid/petroleum ether b.p. 62°-68°C. and eluting with ethyl acetate; recrystallization from petroleum ether b.p. 80°-100°C. gave 2-[4-(2,4-difluorophenoxy)phenyl] propionic acid, m.p. 105°-106°C.

Workup

  1. additionadded
  2. extractionThe cooled solid was extracted with methylene chloride containing a little dilute hydrochloric acid
  3. filtrationfiltered
  4. extractionthe solution extracted with dilute potassium carbonate solution
  5. extractionThe aqueous extract
  6. washwas washed with ether
  7. customthe resulting oil was isolated in ether
  8. customevaporated to dryness
  9. customThe resulting solid was purified by preparative layer chromatography
  10. washeluting with ethyl acetate
  11. customrecrystallization from petroleum ether b.p. 80°-100°C.

Sources & evidence

ORD record
ord-f5375500ca6c4d54816e503939ed4c14
Source dataset
uspto-grants-1976_09
Patent number
US03981905

Reaction notes

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