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

HRID 2232748Notes

Reaction equation

HRID 2232748 reaction equation
C([O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[CH:7]=[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])C.[OH-].[Na+]>CO>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])=[CH:7]/[CH:6]=[CH:5]/[C:4]([OH:23])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742562(E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347238(E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acidYield 93.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As before, (E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester (1.7 g) in methanol (15 mL) was carried out using 4N sodium hydroxide (2.5 mL). After acidification, the product was extracted into dichloromethane (2×50 mL). The combined extracts were dried and evaporated and the residue crystallized from ether-hexane to provide 1.45 g of (E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid, mp 159°-160° C.

Workup

  1. extractionAfter acidification, the product was extracted into dichloromethane (2×50 mL)
  2. customThe combined extracts were dried
  3. customevaporated
  4. customthe residue crystallized from ether-hexane

Sources & evidence

ORD record
ord-9e71ae8220af43f8864a2d94ac929951
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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