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

HRID 1110503Notes

Reaction equation

HRID 1110503 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. Anal. Calculated for C17H12F2O2 : C, 71.32: H, 4.22; F, 13.27 Found: C, 71.48; H, 4.22; F, 13.53.

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-c3437b6bc64d4023a1ee306e6564fc1d
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

Loading…