Sodium Hydroxide → (E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid

HRID 2232758Notes

Reaction equation

HRID 2232758 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]=[C:18]([Cl:22])[CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)C.[OH-].[Na+]>CO>[Cl:15][C:11]1[CH:10]=[C:9]([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:7]/[CH:6]=[CH:5]/[C:4]([OH:23])=[O:3])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14347255(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester

Product 1

HCID 14347243(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester (10.5 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 furnish 8.95 g of (E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid, mp 167°-68° C. Recrystallization from ether-hexane gave the analytical specimen, mp 167°-168° 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-c849ba63e3424a2b923b088f1398cdf3
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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