(E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester → (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid

HRID 2232760Notes

Reaction equation

HRID 2232760 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]([Cl:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)C>CO.[OH-].[Na+]>[Cl:15][C:12]1[CH:11]=[CH:10][C:9]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([Cl: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 1

HCID 14347256(E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347245(E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid ethyl ester (7.5 g) in methanol (30 mL) and 2N sodium hydroxide solution (15 mL) was heated at reflux for 30 minutes. The crude solid obtained from the usual work up, was crystallized from ether-hexane to yield 6.55 g of (E)-5,5-bis(4-chlorophenyl)-2,4-pentadienoic acid, mp 213°-215° C. Recrystallization of a portion from 2-propanol furnished the analytical sample, mp 214°-215° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. customThe crude solid obtained from the usual work up,
  4. customwas crystallized from ether-hexane

Sources & evidence

ORD record
ord-9fe4fb2b06c94f23bf0f328aac46bcb6
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

Loading…