Sodium Hydroxide → (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid

HRID 2232751Notes

Reaction equation

HRID 2232751 reaction equation
C([O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[CH:7]=[C:8]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)C.[OH-].[Na+]>CO>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)=[CH:7]/[CH:6]=[CH:5]/[C:4]([OH:23])=[O:3])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14347252(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347251(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid ethyl ester (8.8 g) in methanol (30 mL) was treated with 2N sodium hydroxide solution (20 mL) and the mixture was heated at reflux for 15 minutes. The crude solid obtained from the usual work up, was crystallized from dichloromethane-hexane to yield 7.5 g of (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid mp 186°-188° C. A portion was recrystallized from ether-hexane to furnish the analytical specimen, mp 187°-188° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 15 minutes
  3. customThe crude solid obtained from the usual work up,
  4. customwas crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-f738310b169c4d5fba64ce4f653a3cf6
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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