Sodium Hydroxide → HCID 21453328, compound

HRID 1076771Notes

Reaction equation

HRID 1076771 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[C:9]([O:11]C)=[O:10])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[C:9]([OH:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21453332HCID 21453332, compound

Product 1

HCID 21453328HCID 21453328, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.5 g. of methyl 2-(2-fluoro-2'-nitro-4-biphenylyl)propionate dissolved in 180 ml. of methanol is treated with 36 ml. of 10% aqueous sodium hydroxide solution at reflux temperature for 1 hour. The mixture is concentrated to remove most of the methanol, chilled and acidified with a mixture of 50 ml. of concentrated HCl and 50 g. of ice. The mixture is extracted four times with methylene chloride, the extract washed with water and dried (Na2SO4). Following removal of solvent, the residue crystallizes and is decolorized with activated carbon and crystallized from ether-pentane. 2-(2-fluoro-2'-nitro-4-biphenylyl)propionic acid crystallizes, m.p. 106°-108°.

Workup

  1. concentrationThe mixture is concentrated
  2. customto remove most of the methanol
  3. temperaturechilled
  4. additionacidified with a mixture of 50 ml
  5. extractionThe mixture is extracted four times with methylene chloride
  6. washthe extract washed with water
  7. dry with materialdried (Na2SO4)
  8. customremoval of solvent
  9. customthe residue crystallizes
  10. customcrystallized from ether-pentane
  11. custom2-(2-fluoro-2'-nitro-4-biphenylyl)propionic acid crystallizes

Sources & evidence

ORD record
ord-b1dc5efc00c84da78874202c9a2c4931
Source dataset
uspto-grants-1976_05
Patent number
US03957861

Reaction notes

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