Sodium Hydroxide → HCID 21566267, compound

HRID 1580286Notes

Reaction equation

HRID 1580286 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15](C)([C:21]([O-])=O)[C:16]([O:18]CC)=[O:17])=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:21])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21566279HCID 21566279, compound

Product 1

HCID 21566267HCID 21566267, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

Ethyl 2-(2', 4'-difluoro-4-biphenylyl)-2-methylmalonate (5.42 g.) was refluxed for 2 hours with a mixture of 2.5N aqueous sodium hydroxide (27 ml.) and ethanol (13.5 ml.). The solution was then evaporated to a small bulk; the solid sodium salt was dissolved in water and the solution acidified with dilute hydrochloric acid. The resulting precipitate of crude 2-(2',4'-difluoro-4-biphenylyl)-2-methylmalonic acid was decarboxylated by heating for 20 minutes at 200°C. The product was purified by preparative layer chromatography using 5% acetic acid/petroleum ether b.p. 60°-80°C. and eluting with ethyl acetate; recrystallisation from petroleum ether b.p. 80°-100°C. gave 2-(2',4'-difluoro-4-biphenylyl)propionic acid, m.p. 125°-127°C.

Workup

  1. customThe solution was then evaporated to a small bulk
  2. dissolutionthe solid sodium salt was dissolved in water
  3. customThe product was purified by preparative layer chromatography
  4. washeluting with ethyl acetate
  5. customrecrystallisation from petroleum ether b.p. 80°-100°C.

Sources & evidence

ORD record
ord-850c186117274f3caf7c30fc5c239066
Source dataset
uspto-grants-1976_01
Patent number
US03932499

Reaction notes

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