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

HRID 1110510Notes

Reaction equation

HRID 1110510 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°-168° C. Recrystallization from ether-hexane gave the analytical specimen, mp 167°-168° C. Anal. Calculated for C17H12Cl2O2 : C, 63.97; H, 3.79; Cl, 22.21 Found: C, 63.93; H, 3.77; Cl, 22.25.

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-1c7d3685dc0e4bcfb8396a3eefabcc5f
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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