Methyl 4-(4'-fluoro-4-biphenylyl)-4-oxo-butyrate → 4-(4'-Fluoro-4-biphenylyl)-4-oxo-butyric acid

HRID 1979139Notes

Reaction equation

HRID 1979139 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 15541120Methyl 4-(4'-fluoro-4-biphenylyl)-4-oxo-butyrate

Product 1

HCID 107308704-(4'-Fluoro-4-biphenylyl)-4-oxo-butyric acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 4-(4′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester (6.08 g, 0.0212 mol) in 6 M hydrochloric acid was refluxed for 22 hours and cooled to room temperature. The solids were filtered and washed with 0.1 M hydrochloric acid. The filter cake was dried under house vacuum (air bleed) to give 5.72 g of 4-(4′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid as a peach colored solid; mp 173.5-175.5° C.

Workup

  1. temperaturewas refluxed for 22 hours
  2. filtrationThe solids were filtered
  3. washwashed with 0.1 M hydrochloric acid
  4. customThe filter cake was dried under house vacuum (air bleed)

Sources & evidence

ORD record
ord-c5d6a9efac8743879cc9d63f2af1bde4
Source dataset
uspto-grants-2001_05
Patent number
US06239288B1

Reaction notes

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