Potassium Hydroxide → HCID 21566271, compound

HRID 1580293Notes

Reaction equation

HRID 1580293 reaction equation
[OH-:1].[K+].[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:13])[CH:11]=[O:12])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1>O.C(O)C.[N+]([O-])([O-])=O.[Ag+]>[Br:3][C:4]1[CH:9]=[C:8]([CH:10]([CH3:13])[C:11]([OH:1])=[O:12])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 21566293HCID 21566293, compound

Product 1

HCID 21566271HCID 21566271, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

Silver nitrate (6.8 g.) in water (8 ml.) was stirred and treated dropwise with a mixture of 13.2 N potassium hydroxide (3.04 ml.) and water (7.3 ml.). The resulting slurry was diluted with ethanol (9 ml.) and a solution of 2-(2-bromo-4'-fluoro-4-biphenylyl)propionaldehyde (5.9 g.) in ethanol (17 ml.) was added slowly. After stirring for 15 minutes, a mixture of 13.2 N potassium hydroxide (1.8 ml.) and water (1.8 ml.) was added over 1 hour, the temperature being maintained at 43°-45°C. The reaction product was then stirred at 40°C. for 30 minutes, filtered, and the filtrate distilled in vacuo to remove the ethanol. The residue was acidified with dilute hydrochloric acid, the resulting oil isolated in ether, and the extract (after conventional washing) evaporated to dryness. Recrystallisation from light petroleum b.p. 80°-100°C. gave 2-(2-bromo-4'-fluoro-4-biphenylyl)propionic acid, m.p. 129°-131°C.

Workup

  1. additionwas added over 1 hour
  2. temperaturethe temperature being maintained at 43°-45°C
  3. stirringThe reaction product was then stirred at 40°C. for 30 minutes
  4. filtrationfiltered
  5. distillationthe filtrate distilled in vacuo
  6. customto remove the ethanol
  7. customthe resulting oil isolated in ether
  8. extractionthe extract
  9. wash(after conventional washing)
  10. customevaporated to dryness
  11. customRecrystallisation from light petroleum b.p. 80°-100°C.

Sources & evidence

ORD record
ord-e8172dfff8b445a2903d4d69c8d801c8
Source dataset
uspto-grants-1976_01
Patent number
US03932499

Reaction notes

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