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

HRID 1110512Notes

Reaction equation

HRID 1110512 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. Anal. Calculated for C17H12Cl2O2 : C, 63.97; H, 3.79; Cl. 22.21 Found: C, 63.80; H, 3.90; Cl, 21.99.

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-56b8a04d912f4b879573f3012812d79f
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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